The Ch··O H-bond as a determining factor in molecular structure

Noncovalent Forces

Volumn , Issue , 2015, Pages 69-105

  Scheiner, Steve ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; HYDROGEN BONDS;

AQUEOUS ENVIRONMENT; AROMATIC RESIDUES; CATALYTIC MECHANISMS; CHEMICAL AND BIOLOGICALS; CHEMICAL PROBLEMS; METHYLTRANSFERASES; POSITIVE CHARGES; SPECTROSCOPIC FEATURES;

PROTEINS;

EID: 84944254851     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-319-14163-3_4     Document Type: Chapter

References (224)

1. Kumler WD (1935) The effect of the hydrogen bond on the dielectric constants and boiling points of organic liquids. J Am Chem Soc 57:600–605
2. Glasstone S (1937) The structure of some molecular complexes in the liquid phase. Trans Faraday Soc 33:200–214
3. Dippy JFJ (1939) The dissociation constants of monocarboxylic acids; their measurement and their significance in theoretical organic chemistry. Chem Rev 25:151–211
4. Marvel CS, Copley MJ, Ginsberg E (1940) Hydrogen bonds involving the C–H link. XI. Effect of structure on bonding of donor and acceptor molecules. J Am Chem Soc 62:3109–3112
5. Huggins ML (1943) The structure of fibrous proteins. Chem Rev 32:195–218
6. Kosolapoff GM, McCullough JF (1951) Comparison of hydrogen bonding abilities of some organic compounds of phosphorus. J Am Chem Soc 73:5392–5393
7. Dougill MW, Jeffrey GA (1953) The structure of dimethyl oxalate. Acta Cryst 6:831–837
8. Parry GS (1954) The crystal structure of uracil. Acta Cryst 7:313–320
9. Huggins CM, Pimentel GC, Shoolery JN (1955) Proton magnetic resonance studies of chloroform in solution: evidence for hydrogen bonding. J Chem Phys 23:1244–1247
10. Pinchas S (1955) Infrared absorption of the aldehydic C–H group. Anal Chem 27:2–6
11. Schneider WG, Bernstein HJ (1956) Molecular association and infra-red spectrum of solid formaldehyde and acetaldehyde. Trans Faraday Soc 52:13–18
12. Pinchas S (1957) Infrared absorption of aldehydic C–H group. Ortho-substituted benzaldehydes. Anal Chem 29:334–339
13. Brown I, Smith F (1960) Liquid-vapour equilibria. X. The systems acetone + nitromethane and acetone + acetonitrile at 45°C. Austr. J Chem 13:30–37
14. Sutor DJ (1962) The C–H…O hydrogen bond in crystals. Nature 195:68–69
15. Sutor DJ (1963) Evidence for the existence of C–H…O hydrogen bonds in crystals. J Chem Soc 1105–1110
16. Allerhand A, Schleyer PvR (1963) A survey of C–H groups as proton donors in hydrogen bonding. J Am Chem Soc 85:1715–1723
17. Pinchas S (1963) Intramolecular hydrogen bonding in o-nitrobenzaldehyde and related compounds. J Phys Chem 67:1862–1865
18. Ferguson G, Tyrrell J (1965) C–H…O hydrogen bonding. Chem Commun 195–196
19. Bednowitz AL, Post B (1966) Direct determination of the crystal structure of β-fumaric acid. Acta Cryst 21:566–571
20. Krimm S (1967) Hydrogen bonding of C–H…O = C in proteins. Science 158:530–531
21. Krimm S, Kuroiwa K (1968) Low temperature infrared spectra of polyglycines and C–H…O= C hydrogen bonding in polyglycine II. Biopolymers 6:401–407
22. Ramachandran GN, Chandrasekharan R (1968) Interchain hydrogen bonds via bound water molecules in the collagen triple helix. Biopolymers 6:1649–1658
23. Forbes WF (1962) The study of hydrogen bonding and related phenomena by spectroscopic methods. Part VII. Intramolecular hydrogen bonding and steric interactions in o-nitrobenzaldehyde and related compounds. Can J Chem 40:1891–1898
24. 2O. J Chem Phys 55:1236–1244
25. van Duijneveldt-van deRijdt JGCM, van Duijneveldt FB (1971) Perturbation calculations on the hydrogen bonds between some first-row atoms. J Am Chem Soc 93:5644–5653
26. Johansson A, Kollman P, Rothenberg S (1972) Hydrogen bonding and the structure of the HF-HCN dimer. Chem Phys Lett 16:123–127
27. Johansson A, Kollman P, Rothenberg S (1972) The electronic structure of the HCN dimer and trimer. Theor Chim Acta 26:97–100
28. Bonchev D, Cremaschi P (1974) C–H group as proton donor by formation of a weak hydrogen bond. Theor Chim Acta 35:69–80
29. 3O+. J Am Chem Soc 97:955–965
30. Vishveshwara S (1978) Ab-initio molecular orbital studies on CH…X hydrogen bonded systems. Chem Phys Lett 59:26–29
31. Frisch MJ, Pople JA, Del Bene JE (1983) Hydrogen bonds between first-row hydrides and acetylene. J Chem Phys 78:4063–4065
32. 2O… HF. Theor Chim Acta 69:491–503
33. 2Se… HCN. J Mol Struct (Theochem) 136:193–199
34. Chattopadhyay S, Plummer PLM (1990) Ab initio studies on the dimer of sulfur dioxide and hydrogen cyanide. J Chem Phys 93:4187–4191
35. 2, and their effect on nuclear magnetic shielding constants. J Mol Struct (Theochem) 491:23–31
36. 2O produced by photolysis of formaldoxime. J Phys Chem A 103:2945–2951
37. Turi L, Dannenberg JJ (1993) Molecular orbital studies of C–H…O H-bonded complexes. J Phys Chem 97:7899–7909
38. 3. Mol Phys 89:1553–1565
39. Simon S, Duran M, Dannenberg JJ (1996) How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J Chem Phys 105:11024–11031
40. Philp D, Robinson JMA (1998) A computational investigation of cooperativity in weakly hydrogen-bonded assemblies. J Chem Soc Perkin Trans II 1643–1650
41. Afonin AV, Vashchenko AV, Takagi T, Kimura A, Fujiwara H (1999) Specific intramolecular interactions C–H…Nin heteroaryl vinyl ethers and heteroaryl vinyl sulfides studied by1H,13C, and15N NMR spectroscopies and by ab initio calculations on molecular structures as well as on nuclear shieldings. Can J Chem 77:416–424
42. Cense JM, Agafonov V, Ceolin R, Ladure P, Rodier N (1994) Crystal and molecular structure analysis of flutamide. Bifurcated helicoidal C–H…O hydrogen bonds. Struct Chem 5:79–84
43. Kim K, Friesner RA (1997) Hydrogen bonding between amino acid backbone and side chain analogues: a high-level ab initio study. J Am Chem Soc 119:12952–12961
44. Hobza P, Spirko V, Selzle HL, Schlag EW (1998) Anti-hydrogen bond in the benzene dimer and other carbon proton donor complexes. J Phys Chem A 102:2501–2504
45. Samanta U, Chakrabarti P, Chandrasekhar J (1998) Ab initio study of energetics of X-H… π (X= N, O, and C) interactions involving a heteroaromatic ring. J Phys Chem A 102:8964–8969
46. Ornstein RL, Zheng Y (1997) Ab initio quantum mechanics analysis of imidazole C–H…O water hydrogen bonding and a molecular mechanics forcefield correction. J Biomol Struct Dyn 14:657–665
47. McCarthy W, Smets J, Adamowicz L, Plokhotnichenko AM, Radchenko ED, Sheina GG, Stepanian SG (1997) Competition between H-bonded and stacked dimers of pyrimidine: IR and theoretical ab-initio study. Mol Phys 91:513–525
48. Kratochvil M, Engkvist O, Sponer J, Jungwirth P, Hobza P (1998) Uracil dimer: potential energy and free energy surfaces. Ab initio beyond Hartree-Fock and empirical potential surfaces. J Phys Chem A 102:6921–6926
49. Shishkin OV, Sponer J, Hobza P (1999) Intramolecular flexibility of DNA bases in adeninethymine and guanine-cytosineWatson-Crick base pairs. J Mol Struct 477:15–21
50. Hobza P, Sponer J (1999) Structure, energetics, and dynamics of nucleic acid base pairs: nonempirical ab initio calculations. Chem Rev 99:3247–3276
51. 4–SH2. J Chem Phys 93:7808–7812
52. Novoa JJ, Whangbo M-H, Williams JM (1990) Ab initio computational study of the C–H… donor and C–H… anion contact interactions in organic donor salts. Mol Cryst Liquid Cryst 181:25–42
53. 4, HCl). Chem Phys Lett 173:107–114
54. 2. J Chem Phys 95:5179–5186
55. Wiberg KB, Waldron RF, Schulte G, Saunders M (1991) Lactones. X-ray crystallographic studies of nonanolactone and tridecanoloactone: nature of CH…O nonbonded interactions. J Am Chem Soc 113:971–977
56. 4 and CN−. Chem Phys Lett 177:483–490
57. 4 with water. J Mol Struct 270:87–97
58. 2O. J Chem Phys 98:3078–3089
59. 1J(CH) couplings in the vicinity of an atom bearing lone pairs. J Phys Chem 98:8858–8861
60. 2O. Chem Phys Lett 251:33–46
61. 4 model complex. Chem Phys Lett 279:140–150
62. 4, and an O–H…O hydrogen bond. Can J Chem 62:606–609
63. Kumpf RA, Damewood JR (1988) Do nitromethane and malonitrile form C–H…O hydrogen bonds? Implications for molecular recognition by crown ethers. J Chem Soc Chem Commun 621–622
64. Neuheuser T, Hess BA, Reutel C, Weber E (1994) Ab initio calculations of supramolecular recognition modes. Cyclic versus noncyclic hydrogen bonding in the formic acid/formamide system. J Phys Chem 98:6459–6467
65. Erickson JA, McLoughlin JI (1995) Hydrogen bond donor properties of the difluoromethyl group. J Org Chem 60:1626–1631
66. Turi L, Dannenberg JJ (1995) Molecular orbital studies of the nitromethane-ammonia complex. An unusually strong C–H…N hydrogen bond. J Phys Chem 99:639–641
67. 3. J Phys Chem 99:6457–6460
68. 3) hydrogen bond be? Chem Phys Lett 266:23–30
69. Boldeskul IE, Tsymbal IF, Ryltsev EV, Latajka Z, Barnes AJ (1997) Reversal of the usual ν(C–H/D) spectral shift of haloforms in some hydrogen-bonded complexes. J Mol Struct 436:167–171
70. Cubero E, Orozco M, Luque FJ (1999) Electron density topological analysis of the C–H…O anti-hydrogen bond in the fluoroform-oxirane complex. Chem Phys Lett 310:445–450
71. Scheiner S (2000) CH···O hydrogen bonding. In: Hargittai M, Hargittai I (eds) Advances in molecular structure research, JAI Press, Stamford, pp 159–207
72. Scheiner S (2005) The CH--O hydrogen bond. A historical account. In: Dykstra C, Frenking G, Kim K, Scuseria G (eds) Theory and applications of computational chemistry: the First 40 years, Elsevier, Amsterdam, p. 831–857
73. Scheiner S (2006) Contribution of CH··X hydrogen bonds to biomolecular structure. In: Grabowski S. J. (ed) Hydrogen bonding—new insights. Springer, pp 263–292
74. Gu Y, Kar T, Scheiner S (1999) Fundamental properties of the CH…O interaction: is it a true hydrogen bond? J Am Chem Soc 121:9411–9422
75. Alkorta I, Rozas I, Elguero J (2000) Effects of fluorine substitution on hydrogen bond interactions. J Fluor Chem 101:233–238
76. Martins JBL, Politi JRS, Braga AD, Gargano R (2006) Complexes of water with the fluoromethanes. Chem Phys Lett 431:51–55
77. 2O complexes. J Phys Chem A 105:7118–7125
78. 3 with dimethyl ether. J Am Chem Soc 124:7490–7498
79. 4. J Mol Struct 976:97–104
80. 3N: evidence for a novel C–H…N hydrogen bond. J Phys Chem A 103:4572–4579
81. Karger N, Amorim da Costa AM, Ribeiro-Claro JA(1999) C–H…Obonded dimers in liquid 4-methoxybenzaldehyde: a study by NMR, vibrational spectroscopy, and ab initio calculations. J Phys Chem A 103:8672–8677
82. Hobza P, Havlas Z (2000) Blue-shifting hydrogen bonds. Chem Rev 100:4253–4264
83. Marques MPM, da Costa AMA, Ribeiro-Claro PJA (2001) Evidence of C–H…O hydrogen bonds in liquid 4-ethoxybenzaldehyde by NMR and vibrational spectroscopies. J Phys Chem A 105:5292–5297
84. Reimann B, Buchhold K, Vaupel S, Brutschy B, Havlas Z, Spirko V, Hobza P (2001) Improper, blue-shifting hydrogen bond betwen fluorobenzene and fluoroform. J Phys ChemA105:5560–5566
85. Hobza P, Havlas Z (2002) Improper, blue-shifting hydrogen bond. Theor ChemAcc 108:325–334
86. Gopi R, Ramanathan N, Sundararajan K (2014) Experimental evidence for blue-shifted hydrogen bonding in the fluoroform–hydrogen chloride complex: a matrix-isolation infrared and ab initio study. J Phys Chem A 118:5529–5539
87. Gu Y, Kar T, Scheiner S (2000) Comparison of the CH…N and CH…O interactions involving substituted alkanes. J Mol Struct 552:17–31
88. Gu Y, Kar T, Scheiner S (2000) Evaluation of the H-bonding properties of CH…O interactions based upon NMR spectra. J Mol Struct (Theochem) 500:441–452
89. Masunov A, Dannenberg JJ, Contreras RH (2001) C–H bond-shortening upon hydrogen bond formation: influence of an electric field. J Phys Chem A 105:4737–4740
90. Pejov L, Hermansson K (2003) On the nature of blueshifting hydrogen bonds: ab initio and density functional studies of several fluoroform complexes. J Chem Phys 119:313–324
91. Qian W, Krimm S (2002) Vibrational spectroscopy of hydrogen bonding: origin of the different behavior of the C–H…O hydrogen bond. J Phys Chem A 106:6628–6636
92. Qian W, Krimm S (2002) C–H…O and O–H…O hydrogen bonding in formic acid dimer structures: a QM/MM study confirms the common origin of their different spectroscopic behavior. J Phys Chem A 106:11663–11671
93. Hermansson K (2002) Blue-shifting hydrogen bonds. J Phys Chem A 106:4695–4702
94. 6. J Am Chem Soc 124:11854–11855
95. Li X, Liu L, Schlegel HB (2002) On the physical origin of blue-shifted hydrogen bonds. J Am Chem Soc 124:9639–9647
96. Alabugin IV, Manoharan M, Peabody S, Weinhold F (2003) Electronic basis of improper hydrogen bonding: a subtle balance of hyperconjugation and rehybridization. J Am Chem Soc 125:5973–5987
97. Alabugin IV, Manoharan M, Weinhold FA(2004) Blue-shifted and red-shifted hydrogen bonds in hypervalent rare-gas FRg–H···Y. J Phys Chem A 108:4720–4730
98. 3 weakly H-bound complexes. Cryospectroscopic and ab initio study. Chem Phys 313:225–243
99. 2 complex. Chin. J Chem 24:887–893
100. Jablonski M (2007) Blue-shifting intramolecular C–H…O(S) contacts in sterically strained systems. J Mol Struct (Theochem) 820:118–127
101. Li AY (2007) Chemical origin of blue- and redshifted hydrogen bonds: intramolecular hyperconjugation and its coupling with intermolecular hyperconjugation. J Chem Phys 126:154102
102. Joseph J, Jemmis ED (2007) Red-, blue-, or no-shift hydrogen bonds: a unified explanation. J Am Chem Soc 129:4620–4632
103. Michielsen B, Herrebout WA, van derVeken BJ (2008) C–H bonds with a positive dipole gradient can form blue-shifting hydrogen bonds: the complex of halothane with methyl fluoride. ChemPhysChem 9:1693–1701
104. n (n = 1,2; Z = O, S, Se, F, Cl, Br; Y = Cl−, Br−). J Mol Struct (Theochem) 862:21–27
105. Karpfen A, Kryachko ES (2009) On the intramolecular origin of the blue shift of A–H stretching frequencies: triatomic hydrides HAX. J Phys Chem A 113:5217–5223
106. Grabowski SJ (2011) Red- and blue-shifted hydrogen bonds: the Bent rule from quantum theory of atoms in molecules perspective. J Phys Chem A 115:12789–12799
107. 1≤n≤3. Chem Phys 310:77–84
108. Kryachko ES, Karpfen A (2006) Theoretical force-field model for blue-shifted hydrogen bonds with fluoromethanes. Chem Phys 329:313–328
109. Karpfen A (2011) Blue-shifted A–H stretching frequencies in complexes with methanol: the decisive role of intramolecular coupling. Phys Chem Chem Phys 13:14194–14201
110. Chandra AK, Zeegers-Huyskens T (2013) Theoretical study of the cooperativity in substituted dimethyl ethers complexed with two water molecules. Red or blue shifts of the ν(CH) vibrations? Chem Phys 410:66–70
111. Donoso-Tauda O, Jaque P, Santos JC (2011) Theoretical analysis based on X–H bonding strength and electronic properties in red- and blue-shifting hydrogen-bonded X–H… π complexes. Phys Chem Chem Phys 13:1552–1559
112. Mo Y, Wang C, Guan L, Braïda B, Hiberty PC, Wu W (2014) On the nature of blueshifting hydrogen bonds. Chemistry. Eur J 20:8444–8452
113. Jabłónski M (2014) Red and blue shifted hydridic bonds. J Comput Chem 35:1739–1747
114. Struble MD, Kelly C, Siegler MA, Lectka T (2014) Search for a strong, virtually “No-Shift” hydrogen bond: a cage molecule with an exceptional OH–F interaction. Angew Chem Int Ed 53:8924–8928
115. Gou Q, Feng G, Evangelisti L, Caminati W (2014) Interaction between Freons and Amines: the C–H···Nweak hydrogen bond in quinuclidine–trifluoromethane. J Phys Chem A 118:737–740
116. Dey A, Mondal SI, Patwari GN (2013) Binary complexes of ammonia with phenylacetylenes: a combined experimental and computational approach to explore multiple minima on intermolecular potentials. Chem Phys Chem 14:746–753
117. Kharat B, Deshmukh V, Chaudhari A (2012) Hydrogen-bonding interactions in acetonitrile oligomers using density functional theory method. Struct Chem 23:637–644
118. Maity S, Dey A, Patwar GN, Karthikeyan S, Kim KS (2010) A combined spectroscopic and abinitio investigation of phenylacetylene-methylamine complex. Observation of σ and π type hydrogen-bonded configurations and fluorescence quenching by weak C–H···N hydrogen bonding. J Phys Chem A 114:11347–11352
119. Howard AA, Tschumper GS, Hammer NI (2010) Effects of hydrogen bonding on vibrational normal modes of pyrimidine. J Phys Chem A 114:6803–6810
120. Jablonski M, Palusiak M (2010) Basis set and method dependence in atoms in molecules calculations. J Phys Chem A 114:2240–2244
121. Liu G, Wang H, Li W (2006) Solvent effect on the type (red-shifted or blue-shifted) of hydrogen bond. J Mol Struct (Theochem) 772:103–108
122. 3 complex. Phys Chem Chem Phys 4:571–576
123. Shirhatti PR, Maity DK, Wategaonkar S (2013) C–H···Y hydrogen bonds in the complexes of p-cresol and p-cyanophenol with fluoroform and chloroform. J Phys ChemA 117:2307–2316
124. Zhang G, He W, Chen D (2014) On difference of properties between organic fluorine hydrogen bond C–H···F–C and conventional hydrogen bond. Mol Phys 112:1736–1744
125. Christenholz CL, Obenchain DA, Peebles RA, Peebles SA (2014) Rotational spectroscopic studies of C–H···F interactions in the vinyl fluoride···difluoromethane complex. J Phys Chem A 118:1610–1616
126. Lu N, Ley RM, Cotton CE, Chung W-C, Francisco JS, Negishi E-I (2013) Molecular tuning of the closed shell C–H···F–C hydrogen bond. J Phys Chem A 117:8256–8262
127. 4 dimers? Mol Phys 110:377–387
128. 3 with HCCH: a test of density functional theory methods. Phys Chem Chem Phys 13:4388–4392
129. Saar BG, O’Donoghue GP, Steeves AH, John W., Thoman J (2006) Evidence for a blue-shifting intramolecular hydrogen bond in the vibrational overtone spectrum of 1H-nonafluorobutane. Chem Phys Lett 417:159–163
130. Favero LB, Giuliano BM, Melandri S, Maris A, Ottaviani P, Velino B, Caminati W (2005) CH…O and CHF links form the cage structure of dioxane-trifluoromethane. J Phys ChemA 109:7402–7404
131. Lu P, Liu G-Q, Li J-C (2005) Existing problems in theoretical determination of red-shifted or blue-shifted hydrogen bond. J. Mol. Struct (Theochem) 723:95–100
132. Domagala M, Grabowski SJ (2010) Hydrocarbons as proton donors in C–H…N and C–H… S hydrogen bonds. Chem Phys 367:1–6
133. Wolstenholme DJ, Weigand JJ, Cameron EM, Cameron TS (2008) The progression of strong and weak hydrogen bonds in a series of ethylenediammonium dithiocyanate derivatives—A new bonding protocol for macromolecules? Phys Chem Chem Phys 10:3569–3577
134. Domagala M, Grabowski SJ (2005) C–H…N and C–H… S hydrogen bonds—influence of hybridization on their strength. J Phys Chem A 109:5683–5688
135. Afonin AV, Toryashinova DD, Schmidt EY (2004) Investigation of C–H…X (X = N, O, S) intramolecular hydrogen bond in 1-vinyl-2-(2’-heteroaryl)pyrroles by ab initio calculations. J Mol Struct (Theochem) 680:127–135
136. 2 and Cl−) complexes predicted by a perturbative model. Chem Phys Lett 424:239–242
137. Hopkins WS, Hasan M, Burt M, Marta RA, Fillion E, McMahon TB (2014) Persistent intramolecular C–H···X (X = O or S) hydrogen-bonding in benzyl meldrum’s acid derivatives. J Phys Chem A 118:3795–3803
138. Tamasi G, Botta F, Cini R (2006) DFT-molecular modeling analysis of C–H…N and C–H… S hydrogen bond type interactions in selected platinum–purine/pyrimidine complexes. J Mol Struct (Theochem) 766:61–72
139. 2CO, as revealed by rotational spectroscopy. Phys Chem Chem Phys 16:12261–12265
140. 2Cl trimer in Xe matrix and calculations of stable isomers by density functional theory. J Mol Struct 1012:43–49
141. Castro M, Nicolas-Vazquez I, Zavala JI, Sanchez-Viesca F, Berros M (2007) Theoretical study of intramolecular CH–X (X = N, O, Cl) hydrogen bonds in thiazole derivatives. J Chem Theory Comput 3:681–688
142. Balamurugan V, Mukherjee J, Hundal MS, Mukherjee R (2007) Supramolecular architectures with ladder and lamellar topologies using metal-ligand coordination units via C–H···Cl and O–H···Cl hydrogen bonding. Struct Chem 18:133–144
143. Pazout R, Houskova J, Dusek M (2011) Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H… I and C–H… I hydrogen bonds. Struct Chem 22:1325–1330
144. Michielsen B, Verlackt C, van der Veken BJ, Herrebout WA (2012) C–H…X (X = S, P) hydrogen bonding: the complexes of halothane with dimethyl sulfide and trimethylphosphine. J Mol Struct 1023:90–95
145. Ramasami P, Ford TA (2012) Ab initio studies of some hydrogen-bonded complexes of fluoroform—evidence for blue-shifted behaviour. J Mol Struct 1023:163–169
146. carbene hydrogen bonds and competing interactions in monoprotonated tripodal carbenes. J Comput Chem 25:649–659
147. Yu F (2013) Intermolecular interactions of formic acid with benzene: energy decomposition analyses with ab initioMP2and double-hybrid density functional computations. Int J Quantum Chem 113:2355–2360
148. Karthikeyan S, Ramanathan V, Mishra BK (2013) Influence of the substituents on the CH… π interaction: benzene–methane complex. J Phys Chem A 117:6687–6694
149. Majumder M, Mishra BK, Sathyamurthy N (2013) CH… π and π… π interaction in benzeneacetylene clusters. Chem Phys 557:59–65
150. Michielsen B, Dom JJJ, van der Veken BJ, Hesse S, Xue Z, Suhm MA, Herrebout WA (2010) The complexes of halothane with benzene: the temperature dependent direction of the complexation shift of the aliphatic C–H stretching. Phys Chem Chem Phys 12:14034–14044
151. Shirhatti PR, Wategaonkar S (2010) Blue shifted hydrogen bond in 3-methylindole·CHX3 complexes (X = Cl, F). Phys Chem Chem Phys 12:6650–6659
152. Takahashi O, Kohno Y, Gondoh Y, Saito K, Nishio M (2003) General preference for alkyl/phenyl folded conformations. Relevance of the CH/π and CH/O interactions to stereochemistry as evidenced by ab initio MO calculations. Bull Chem Soc Jpn 76:369–374
153. Xu X, Pooi B, Hirao H, Hong SH (2014) CH–π and CF–π interactions lead to structural changes of N-heterocyclic carbene palladium complexes. Angew Chem Int Ed 53:1283–1287
154. Wang Y, Balbuena PB (2001) Associations of alkyl carbonates: intermolecular C–H…O interactions. J Phys Chem A 105:9972–9982
155. Wetmore SD, Schofield R, Smith DM, Radom L (2001) A theoretical investigation of the effects of electronegative substitution on the strength of C–H…N hydrogen bonds. J Phys Chem A 105:8718–8726
156. Kar T, Scheiner S (2004) Comparison of cooperativity in CH··O and OH··O hydrogen bonds. J Phys Chem A 108:9161–9168
157. Malenov DP, Janjic GV, Veljkovic DŽ, Zaric SD (2013) Mutual influence of parallel, CH/O, OH/π and lone pair/π interactions in water/benzene/water system. Comput. Theor. Chem 1018:59–65
158. Gao X, Liu Y, Li H, Bian J, Zhao Y, Cao Y, Mao Y, Li X, Xu Y, Ozaki Y, Wu J (2013) A cooperative hydrogen bonding system with a C–H…O hydrogen bond in ofloxacin. J Mol Struct 1040:122–128
159. Lee K-M, Chen JCC, Chen H-Y, Lin IJB (2012) A triple helical structure supported solely by C–H…O hydrogen bonding. Chem Commun 48:1242–1244
160. 3CX···NCH(CNH)···NCH(CNH) complexes (X = Cl, Br). Mol Phys 109:1641–1648
161. Samanta AK, Pandey P, Bandyopadhyay B, Chakraborty T (2010) Cooperative strengthening of an intramolecularO–H···Ohydrogen bond by a weakC–H···Ocounterpart: matrix-isolation infrared spectroscopy and quantum chemical studies on 3-methyl-1,2-cyclohexanedione. J Phys Chem A 114:1650–1656
162. 2O complex. J Phys Chem A 111:10166–10169
163. Scheiner S, Kar T (2005) Effect of solvent upon CH··O hydrogen bonds with implications for protein folding. J Phys Chem B 109:3681–3689
164. Shi Z, Olson CA, Bell AJ, Kallenbach NR (2002) Non-classical helix-stabilizing interactions: C–H…O H-bonding between Phe and Glu side chains in α-helical peptides. Biophys Chem 101–102:267–279
165. αH.O hydrogen bond of amino acid residues. J Biol Chem 276:9832–9837
166. Scheiner S (2005) Relative strengths of NH··O and CH··O hydrogen bonds between polypeptide chain segments. J Phys Chem B 109:16132–16141
167. Scheiner S (2007) The strength with which a peptide group can form a hydrogen bond varies with the internal conformation of the polypeptide chain. J Phys Chem B 111:11312–11317
168. Adhikari U, Scheiner S (2013) Preferred configurations of peptide-peptide interactions. J Phys Chem A 117:489–496
169. Scheiner S (2006) Contributions of NH··O and CH··O H-bonds to the stability of β-sheets in proteins. J Phys Chem B 110:18670–18679
170. Vener MV, Egorova AN, Fomin DP, Tsirelson VG (2007) QTAIM study of the closed-shell interactions in peptide secondary structures: a cluster treatment of oligo- and polyalanines. Chem Phys Lett 440:279–285
171. Parthasarathi R, Raman SS, Subramanian V, Ramasami T (2007) Bader’s electron density analysis of hydrogen bonding in secondary structural elements of proteins. J Phys Chem A 111:7141–7148
172. Guo H, Gorin A, Guo H (2009) A peptide-linkage deletion procedure for estimate of energetic contributions of individual peptide groups in a complex environment: application to parallel β-sheets. Interdiscip Sci Comput Life Sci 1:12–20
173. Vener MV, Egorova AN, Fomin DP, Tsirel’son VG (2009) A quantum-topological analysis of noncovalent interactions in secondary polyalanine structures. Russ. J Phys Chem B 3:541–547
174. LaPointe SM, Farrag S, Bohórquez HJ, Boyd RJ (2009) QTAIM study of an α-helix hydrogen bond network. J Phys Chem B 113:10957–10964
175. α–H…O = C hydrogen bonds in transmembrane protein. J Phys Chem B 112:1041–1048
176. Pohl G, Plumley JA, Dannenberg JJ (2013) The interactions of phenylalanines in β-sheet-like structures from molecular orbital calculations using density functional theory (DFT), MP2, and CCSD(T) methods. J Chem Phys 138:245102
177. Hussain S, Das G, Chaudhuri MK (2007) Intermolecular hydrogen bonded and self-assembled β-pleated sheet structures of β-sulfidocarbonyls. J Mol Struct 837:190–196
178. Adhikari U, Scheiner S (2013) First Steps in growth of a polypeptide toward β-sheet structure. J Phys Chem B 117:11575–11583
179. Scheiner S, Kar T, Pattanayak J (2002) Comparison of various types of hydrogen bonds involving aromatic amino acids. J Am Chem Soc 124:13257–13264
180. Chang H-C, Lee KM, Jiang J-C, Lin M-S, Chen J-S, Lin IJB, Lin SH (2002) Charge-enhanced C–H…O interactions of a self-assembled triple helical spine probed by high-pressure. J Chem Phys 117:1723–1728
181. Raymo FM, Bartberger MD, Houk KN, Stoddart JF (2001) The magnitude of [C–H… O] hydrogen bonding in molecular and supramolecular assemblies. J Am Chem Soc 123:9264–9267
182. Guo H, Beahm RF, Guo H (2004) Stabilization and destabilization of the Cδ–H…O = C hydrogen bonds involving proline residues in helices. J Phys Chem B 108:18065–18072
183. Deakyne CA, Meot-Ner M (1999) Ionic hydrogen bonds in bioenergetics. Interaction energies of acetylcholine with aromatic and polar molecules. JAmChem Soc 121:1546–1557
184. Cannizzaro CE, Houk KN (2002) Magnitude and chemical consequences of R3N+ –C–H…O= C hydrogen bonding. J Am Chem Soc 124:7163–7169
185. Liu T, Gu J, Tan X-J, Zhu W-L, Luo X-M, Jiang H-L, Ji R-Y, Chen K-X, Silman I, Sussman JL (2002) The relationship between binding models of TMA with furan and imidazole and the molecular electrostatic potentials: DFT and MP2 computational studies. J Phys Chem A 106:157–164
186. Shishkin OV, Palamarchuk GV, Gorb L, Leszczynski J (2008) Opposite charges assisted extra strong C–H…Ohydrogen bond in protonated 2’-deoxyadenosine monophosphate. Chem Phys Lett 452:198–205
187. Adhikari U, Scheiner S (2013) The magnitude and mechanism of charge enhancement of CH··O H-bonds. J Phys Chem A 117:10551–10562
188. Horowitz S, Dirk LMA, Yesselman JD, Nimtz JS, Adhikari U, Mehl RA, Scheiner S, Houtz RL, Al-Hashimi HM, Trievel RC (2013) Conservation and functional importance of carbon-oxygen hydrogen bonding in AdoMet-dependent methyltransferases. JAm Chem Soc 135:15536–15548
189. Kraut J (1977) Serine proteases: structure and mechanism of catalysis. Ann Rev Biochem 46:331–358
190. Wang JH (1970) Directional character of proton transfer in enzyme catalysis. Proc Natl Acad Sci U S A 66:874–881
191. Topf M, Várnai P, Richards WG (2002) Ab initio QM/MM dynamics simulation of the tetrahedral intermediate of serine proteases: insights into the active site hydrogen-bonding network. J Am Chem Soc 124:14780–14788
192. ε–H…O=C< hydrogen bond in the active sites of serine hydrolases. J Mol Biol 241:83–93
193. Ishida T, Kato S (2003) Theoretical perspectives on the reaction mechanism of serine proteases: the reaction free energy profiles of the acylation process. J Am Chem Soc 125:12035–12048
194. 1–H…O=C H-bond: proposal for reaction-driven ring flip mechanism in serine protease catalysis. Proc Natl Acad Sci U S A 97:10371–10376
195. Bachovchin WW (2001) Contributions of NMR spectroscopy to the study of hydrogen bonds in serine protease active sites. Magn Reson Chem 39:39S199–S213
196. Scheiner S (2008) Analysis of catalytic mechanism of serine proteases. Viability of ring-flip hypothesis. J Phys Chem B 112:6837–6846
197. Chen F, Selvam L, Wang F (2010) Blue shifted intramolecular C–H···O improper hydrogen bonds in conformers of zidovudine. Chem Phys Lett 493:358–363
198. Zierke M, Smieško M, Rabbani S, Aeschbacher T, Cutting B, Allain FH-T, Schubert M, Ernst B (2013) Stabilization of branched oligosaccharides: Lewis benefits from a nonconventional C–H···O hydrogen bond. J Am Chem Soc 135:13464–13472
199. Zgarbová M, Jurecka P, Banás P, Otyepka M, Sponer JE, Leontis NB, Zirbel CL, Sponer J (2011) Noncanonical hydrogen bonding in nucleic acids. benchmark evaluation of key basephosphate interactions in folded RNA molecules using quantum-chemical calculations and molecular dynamics simulations. J Phys Chem A 115:11277–11292
200. Shishkin OV, Palamarchuk GV, Gorb L, Leszczynski J (2006) Intramolecular hydrogen bonds in canonical 2’-deoxyribonucleotides: an atoms in molecules study. J Phys Chem B 110:4413–4422
201. Shishkin OV, Gorb L, Zhikol OA, Leszczynski J (2004) Conformational analysis of canonical 2-deoxyribonucleotides. Pyrimidine nucleotides. J Biomol Struct Dyn 21:537–554
202. Alkorta I, Elguero J (2003) Interaction of protein backbone with nucleic acid bases. J Phys Chem B 107:5306–5310
203. Liu Z, Wang G, Li Z, Wang R (2008) Geometrical preferences of the hydrogen bonds on protein-ligand binding interface derived from statistical surveys and quantum mechanics. J Chem Theory Comput 4:1959–1973
204. Hildebrand PW, Günther S, Goede A, Forrest L, Frömmel C, Preissner R (2008) Hydrogenbonding and packing features of membrane proteins: functional implications. Biophys J 94:1945–1953
205. α–H hydrogen bonds. Proc Natl Acad Sci U S A 111:E888–E895
206. Fulara A, Dzwolak W (2010) Bifurcated hydrogen bonds stabilize fibrils of poyl(L-glutamic) acid. J Phys Chem B 114:8278–8283
207. Panigrahi SK, Desiraju GR (2007) Strong and weak hydrogen bonds in the protein-ligand interface. Proteins 67:128–141
208. α···O = C hydrogen bonds. J Am Chem Soc 132:7709–7719
209. Venugopalan P, Kishore R (2013) Unusual folding propensity of an unsubstituted β, γ-hybrid model peptide: importance of the C–H…O intramolecular hydrogen bond. Chem Eur J 19:9908–9915
210. Sukumar N, Mathews FS, Langan P, Davidson VL (2010) A joint x-ray and neutron study on amicyanin reveals the role of protein dynamics in electron transfer. Proc Natl Acad Sci U S A 107:6817–6822
211. Chen JC-H, Hanson BL, Fisher SZ, Langan P, Kovalevsky AY (2012) Direct observation of hydrogen atom dynamics and interactions by ultrahigh resolution neutron protein crystallography. Proc Natl Acad Sci U S A 109:15301–15306
212. Yoneda Y, Mereiter K, Jaeger C, Brecker L, Kosma P, Rosenau T, French A (2008) van der Waals versus hydrogen-bonding forces in a crystalline analog of cellotetraose: cyclohexyl 4’-O-cyclohexyl β-D-cellobioside cylohexane solvate. J Am Chem Soc 130:16678–16690
213. Banks JW, Batsanov AS, Howard JAK, O’Hagan D, Rzepa HS, Martin-Santamaria S (1999) The preferred conformation of α-fluoroamides. J Chem Soc Perkin Trans II 2409–2411
214. Tormena CF, Amadeu NS, Rittner R, Abraham RJ (2002) Conformational analysis in Nmethylfluoroamides. A theoretical, NMR and IR investigation. J Chem Soc Perkin Trans II 773–778
215. Jones CR, Baruah PK, Thompson AL, Scheiner S, Smith MD (2012) Can aC–H···Ointeraction be a determinant of conformation. J Am Chem Soc 134:12064–12071
216. 2O complex. Chem Phys Chem 15:918–923
217. Huang Z, Chen Z, Lim LH, Quang GCP, Hirao H, Zhou JS (2013) Weak arene C–H…O hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones. Angew Chem Int Ed 52:5807–5812
218. Huang Z, Lim LH, Chen Z, Li Y, Zhou F, Su H, Zhou JS (2013) Arene CH–O hydrogen bonding: a stereocontrolling tool in palladium-catalyzed arylation and vinylation of ketones. Angew Chem Int Ed 52:4906–4911
219. Juribasic M, Bellotto L, Tusek-Bozic L (2012) N–H···O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters. Struct Chem 23:257–266
220. You L-Y, Chen S-G, Zhao X, Liu Y, Lan W-X, Zhang Y, Lu H-J, Cao C-Y, Li Z-T (2012) C–H…O hydrogen bonding induced triazole foldamers: efficient halogen bonding receptors for organohalogens. Angew Chem Int Ed 51:1657–1661
221. Lippert KM, Hof K, Gerbig D, Ley D, Hausmann H, Guenther S, Schreiner PR (2012) Hydrogen-bonding thiourea organocatalysts: The privileged 3,5-bis(trifluoromethyl)phenyl group. Eur J Org Chem 2012:5919–5927
222. Bandyopadhyay B, Pandey P, Banerjee P, Samanta AK, Chakraborty T (2012) CH···O interaction lowers hydrogen transfer barrier to keto-enol tautomerization of β-cyclohexanedione: combined infrared spectroscopic and electronic structure calculation study. J Phys Chem A 116:3836–3845
223. Vibhute AM, Gonnade RG, Swathi RS, Sureshan KM (2012) Strength from weakness: opportunistic CH.O hydrogen bonds differentially dictate the conformational fate in solid and solution states. Chem Commun 48:717–719
224. Solà J, Riera A, Verdaguer X, Maestro MA (2005) Phosphine-substrate recognition through the C–H…O hydrogen bond: application to the asymmetric Pauson-Khand reaction. J Am Chem Soc 127:13629–13633