Vibrational circular dichroism spectroscopy of chiral molecules

Topics in Current Chemistry

Volumn 298, Issue , 2011, Pages 189-236

  Yang, Guochun ^a   Xu, Yunjie ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Absolute configuration and conformation determinations; Density functional theory; Induced solvent chirality; Transient VCD measurements; Vibrational circular dichroism

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATION; METHODOLOGY; QUANTUM THEORY; STEREOISOMERISM;

CIRCULAR DICHROISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; STEREOISOMERISM;

EID: 79951832227     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2010_86     Document Type: Article

References (183)

1. Barron LD (2004) Molecular light scattering and optical activity, 2nd edn. Cambridge University Press, Cambridge
2. Polavarapu PL (1998) Vibrational spectra: principles and applications with emphasis on optical activity. Elsevier, New York
3. Holzwarth G, Hsu EC, Mosher HS et al (1974) Infrared circular dichroism of carbon-hydrogen and carbon-deuterium stretching modes. J Am Chem Soc 96:251-252
4. Nafie LA, Cheng JC, Stephens PJ (1975) Vibrational circular dichroism of 2,2,2-trifluoro-1-phenylethanol. J Am Chem Soc 97:3842-3843
5. Galwas PA (1983) On the distribution of optical polarization in molecules. PhD Thesis, University of Cambridge, Cambridge
6. Buckingham AD, Fowler PW, Galwas PA (1987) Velocity-dependent property surfaces and the theory of vibrational circular-dichroism. Chem Phys 112:1-14
7. Stephens PJ (1985) Theory of vibrational circular-dichroism. J Phys Chem 89:748-752
8. Stephens PJ, Lowe MA (1985) Vibrational circular-dichroism. Annu Rev Phys Chem 36:213-241
9. Stephens PJ (1987) Gauge dependence of vibrational magnetic dipole transition moments and rotational strengths. J Phys Chem 91:1712-1715
10. Nafie LA (1983) Adiabatic molecular-properties beyond the Born-Oppenheimer approximation - complete adiabatic wave-functions and vibrationally induced electronic current-density. J Chem Phys 79:4950-4957
11. Nafie LA (1992) Velocity-gauge formalism in the theory of vibrational circular-dichroism and infrared-absorption. J Chem Phys 96:5687-5702
12. Nafie LA (1997) Electron transition current density in molecules.1. Non-Born-Oppenheimer theory of vibronic and vibrational transitions. J Phys Chem A 101:7826-7833 (Pubitemid 127591244)
13. Freedman TB, Shih M-L, Lee E et al (1997) Ab initio calculations for vibrational transitions in ethylene and formaldehyde. J Am Chem Soc 119:10620-10626
14. Stephens PJ, Devlin FJ (2000) Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 12:172-179 (Pubitemid 30253630)
15. Polavarapu PL (2006) Quantum mechanical predictions of chiroptical vibrational properties. Int J Quantum Chem 106:1809-1814
16. Freedman TB, Cao XL, Dukor RK et al (2003) Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 15:743-758 (Pubitemid 37356644)
17. Polavarapu PL, He J (2004) Chiral analysis using mid-IR vibrational CD spectroscopy. Anal Chem 76:61A-67A (Pubitemid 38166549)
18. Polavarapu PL (2007) Renaissance in chiroptical spectroscopic methods for molecular structure determination. Chem Rec 7:125-136
19. Stephens PJ, Devlin FJ, Pan JJ (2008) The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality 20:643-663 (Pubitemid 351656169)
20. Stephens PJ, Devlin FJ, Aamouche A (2002) Determination of the structures of chiral molecules using vibrational circular dichroism spectroscopy. In: Hicks JM (ed) Chirality: physical chemistry. ACS Symposium Series, vol. 810, Chap. 2, Oxford University Press, New York, pp 18-33 (Pubitemid 135693044)
21. Yang GC, Ha T, Fan E et al (2010) Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory. Chirality 22:734-743
22. Yang GC, Xu Y, Hou JB et al (2010) Determination of the absolute configuration of pentacoordinate chiral phosphorus compounds in solution by using vibrational circular dichroism spectroscopy and density functional theory. Chem Eur J 16:2518-2527
23. n] (n = 0 ~ 3, tfac = 3-trifluoroacetylcam-phorato and acac = acetylacetonato). Inorg Chem 48:4354-4361
24. Nafie LA (2008) Vibrational circular dichroism: a new tool for the solution-state determination of the structure and absolute configuration of chiral natural product molecules. Nat Prod Commun 3:451-466
25. Brotin T, Cavagnat D, Dutasta JP et al (2006) Vibrational circular dichroism study of optically pure cryptophane-A. J Am Chem Soc 128:5533-5540
26. Devlin FJ, Stephens PJ, Besse P (2005) Are the absolute configurations of 2-(1-hydro-xyethyl)-chromen-4-one and its 6-bromo derivative determined by X-ray crystallography correct? A vibrational circular dichroism study of their acetate derivatives. Tetrahedron Asymmetry 16:1557-1566
27. Nafie LA (2004) New approaches to the determination of absolute configuration for Chiral Pharmaceuticals (Business Briefing - PharmaTech
28. Jeffrey GA, Saenger W (1991) Hydrogen bonding in biological structure. Springer-Verlag, Berlin
29. Nafie LA, Keiderling TA, Stephens PJ (1976) Vibrational circular-dichroism. J Am Chem Soc 98:2715-2723
30. Nafie LA (1988) Polarization modulation FTIR spectroscopy. In: Mackenzie MW (ed) Advances in applied FTIR spectroscopy. Wiley, New York, pp 67-104
31. Nafie LA, Long F, Freedman TB et al (1998) The determination of enantiomeric purity and absolute configuration by vibrational circular dichroism spectroscopy. In: de Haseth JA (ed) Fourier transform spectroscopy: 11th International Conference, vol. 430, American Institute of Physics. Woodbury, New York, pp 432-434
32. Dukor RK, Nafie LA (2000) Vibrational optical activity of pharmaceuticals and biomole-cules. In: Meyers RA (ed) Encyclopaedia of analytical chemistry: instrumentation and applications. Wiley, Chichester, UK, pp 662-676
33. Nafie LA, Diem M (1979) Theory of high-frequency differential interferometry - application to the measurement of infrared circular and linear dichroism via Fourier-transform spectroscopy. Appl Spectrosc 33:130-135 (Pubitemid 9443363)
34. Nafie LA, Diem M, Vidrine DW (1979) Fourier-transform infrared vibrational circular-dichroism. J Am Chem Soc 101:496-498
35. Lipp ED, Zimba CG, Nafie LA (1982) Vibrational circular-dichroism in the mid-infrared using Fourier-transform spectroscopy. Chem Phys Lett 90:1-5
36. Nafie LA (2000) Dual polarization modulation: a real-time, spectral-multiplex separation of circular dichroism from linear birefringence spectral intensities. Appl Spectrosc 54: 1634-1645 (Pubitemid 32074750)
37. Malon P, Keiderling TA (1988) A solution to the artifact problem in Fourier-transform vibrational circular-dichroism. Appl Spectrosc 42:32-38 (Pubitemid 18560215)
38. Polavarapu PL (1989) New developments in Fourier-transform infrared vibrational circular-dichroism measurements. Appl Spectrosc 43:1295-1297 (Pubitemid 20643948)
39. Malon P, Keiderling TA (1996) Spinning quarter-wave plate polarization modulator: test of feasibility for vibrational circular dichroism measurements. Appl Spectrosc 50:669-674 (Pubitemid 126595717)
40. Malon P, Keiderling TA (1997) Theoretical simulation of a polarization modulator based on mechanical rotation of a polarizing element. Appl Opt 36:6141-6148 (Pubitemid 128484540)
41. Cao XL, Dukor RK, Nafie LA (2008) Reduction of linear birefringence in vibrational circular dichroism measurement: use of a rotating half-wave plate. Theor Chem Acc 119:69-79
42. Hug W (2003) Virtual enantiomers as the solution of optical activity's deterministic offset problem. Appl Spectrosc 57:1-13
43. Nafie LA, Buijs H, Rilling A et al (2004) Dual source Fourier transform polarization modulation spectroscopy: an improved method for the measurement of circular and linear dichroism. Appl Spectrosc 58:647-654
44. Cao X, Shah RD, Dukor RK et al (2004) Extension of Fourier transform vibrational circular dichroism into the near-infrared region: continuous spectral coverage from 800 to 10 000 cm (-1). Appl Spectrosc 58:1057-1064
45. Guo C, Shah RD, Dukor RK et al (2006) Fourier transform vibrational circular dichroism from 800 to 10000 cm(-1): near-IR-VCD spectral standards for terpenes and related molecules. Vib Spectrosc 42:254-272 (Pubitemid 44767983)
46. Keiderling TA, Kubelka J, Hilario J (2006) Contribution of transition dipole coupling to amide coupling in IR spectra of peptide secondary structures. Vibrational Spectroscopy of Biological and Polymer Materials 253-324
47. Lakhani A, Malon P, Keiderling TA (2009) Appl Spectrosc 63:755-785
48. Losada M, Xu Y (2007) Chirality transfer through hydrogen-bonding: experimental and ab initio analyses of vibrational circular dichroism spectra of methyl lactate in water. Phys Chem Chem Phys 9:3127-3135
49. Bose PK, Polavarapu PL (1999) Vibrational circular dichroism is a sensitive probe of the glycosidic linkage: oligosaccharides of glucose. J Am Chem Soc 121:6094-6095 (Pubitemid 29305159)
50. Shanmugam G, Polavarapu PL (2004) Structure of A beta (25-35) peptide in different environments. Biophys J 87:622-630 (Pubitemid 38880114)
51. Shanmugam G, Polavarapu PL, Gopinath D, Jayakumar R (2005) The structure of antimicrobial pexiganan peptide in solution probed by Fourier transform infrared absorption, vibrational circular dichroism, and electronic circular dichroism spectroscopy. Biopolymers 80:636-642 (Pubitemid 41665233)
52. Shanmugam G, Polavarapu PL (2004) Vibrational circular dichroism spectra of protein films: thermal denaturation of bovine serum albumin. Biophys Chem 111:73-77 (Pubitemid 39140860)
53. Shanmugam G, Polavarapu PL (2005) Film techniques for vibrational circular dichroism measurements. Appl Spectrosc 59:673-681 (Pubitemid 40680321)
54. Petrovic AG, Bose PK, Polavarapu PL (2004) Vibrational circular dichroism of carbohydrate films formed from aqueous solutions. Carbohydr Res 339:2713-2720 (Pubitemid 39425142)
55. Petrovic AG, Polavarapu PL (2005) Structural transitions in polyriboadenylic acid induced by the changes in pH and temperature: vibrational circular dichroism study in solution and film states. J Phys Chem B 109:23698-23705 (Pubitemid 43081545)
56. Shanmugam G, Polavarapu PL, Kendall LA et al (2005) Structures of plant viruses from vibrational circular dichroism. J Gen Virol 86:2377-2384
57. Haraday T, Kuroday R (2002) Circular dichroism measurement of a protein in dried thin films. Chem Lett 326-327
58. Merten C, Kowalik T, Hartwig A (2008) Vibrational circular dichroism spectroscopy of solid polymer films: effects of sample orientation. Appl Spectrosc 62:901-905
59. Buffeteau T, Lagugne-Labarthet F, Sourisseau C (2005) Vibrational circular dichroism in general anisotropic thin solid films: measurement and theoretical approach. Appl Spectrosc 59:732-745 (Pubitemid 40891136)
60. Cohan NV, Hameka HF (1966) Isotope effects in optical rotation. J Am Chem Soc 88:2136-2142
61. Faulkner TR, Marcott C, Moscowitz A et al (1977) Anharmonic effects in vibrational circular-dichroism. J Am Chem Soc 99:8160-8168
62. Nafie LA, Walnut TH (1977) Vibrational circular-dichroism theory - localized molecular-orbital model. Chem Phys Lett 49:441-446
63. Walnut TH, Nafie LA (1977) IR absorption and born-oppenheimer approximation. 2. Vibrational circular-dichroism. J Chem Phys 67:1501-1510
64. Nafie LA, Freedman TB (1983) Vibronic coupling theory of infrared vibrational transitions. J Phys Chem 78:7108-7116
65. Dutler R, Rauk A (1989) Calculated infrared-absorption and vibrational circular-dichroism intensities of oxirane and its deuterated analogs. J Am Chem Soc 111:6957-6966
66. Yang D, Rauk A (1992) Vibrational circular dichroism intensities: ab initio vibronic coupling theory using the distributed origin gauge. J Chem Phys 97:6517-6534
67. Hunt KLC, Harris RA (1991) Vibrational circular-dichroism and electric-field shielding tensors - a new physical interpretation based on nonlocal susceptibility densities. J Chem Phys 94:6995-7002
68. Lazzeretti P, Malagoli M, Zanasi R (1991) Electromagnetic moments and fields induced by nuclear vibrational motion in molecules. Chem Phys Lett 179:297-302
69. Hansen AE, Stephens PJ, Bouman TD (1991) Theory of vibrational circular-dichroism - formalisms for atomic polar and axial tensors using noncanonical orbitals. J Phys Chem 95:4255-4262
70. 2S. Chem Phys Lett 108:185-190
71. Yamaguchi Y, Frisch M, Gaw J et al (1986) Analytic evaluation and basis set dependence of intensities of infrared-spectra. J Chem Phys 84:2262-2278
72. Cheeseman JR, Frisch MJ, Devlin FJ et al (1996) Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 252:211-220 (Pubitemid 126165521)
73. Nicu VP, Neugebauer J, Baerends EJ (2008) Effects of complex formation on vibrational circular dichroism spectra. J Phys Chem A 112:6978-6991
74. Nicu VP, Baerends EJ (2009) Robust normal modes in vibrational circular dichroism spectra. Phys Chem Chem Phys 11:6107-6118
75. Cichewicz RH, Clifford LJ, Lassen PR, Cao X, Freedman TB, Nafie LA, Deschamps JD, Kenyon VA, Flanary JR, Holman TR, Crews P (2005) Stereochemical determination and bioactivity assessment of (S)-(1)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorg Med Chem 13: 5600-5612 (Pubitemid 41187923)
76. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C,Ochterski JW, Ayala PY, Morokuma K,Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD,Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03 C02
77. Kuppens T, Langenaeker W, Tollenaere JP et al (2003) Determination of the stereochemistry of 3-hydroxymethyl-2, 3-dihydro-[1, 4]dioxino[2, 3-b]pyridine by vibrational circular dichro-ism and the effect of DFT integration grids. J Phys Chem A 107:542-553
78. Pacios LF, Galvez O, Gomez PC (2005) Variation of geometries and electron properties along proton transfer in strong hydrogen-bond complexes. J Chem Phys 122:214307
79. Sadlej J, Dobrowolski JC, Rode JE et al (2006) DFT study of vibrational circular dichroism spectra of D-lactic acid-water complexes. Phys Chem Chem Phys 8:101-113
80. Pathak AK, Mukherjee T, Maity DK (2007) Structure, energy, and IR spectra of I-2(center dot-).nH(2)O clusters (n = 1-8): a theoretical study. J Chem Phys 126:034301
81. Nibu Y, Marui R, Shimada H (2006) IR spectroscopy of hydrogen-bonded 2-fluoropyridine-methanol clusters. J Phys Chem A 110:12597-12602 (Pubitemid 46063792)
82. Boys SF, Bernardi F (1970) Calculation of small molecular interactions by differences of separate total energies - some procedures with reduced errors. Mol Phys 10:553-559
83. Becke AD (1993) Density-functional thermochemistry. 3. The role of exact exchange. J Chem Phys 9:5648-5652
84. Lee CT, Yang WT, Parr RG (1988) Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Phys Rev B Condens Matter 37:785-789
85. Stephens PJ, Devlin FJ, Chabalowski CF et al (1994) Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields. J Phys Chem 98:11623-11627
86. Kuppens T, Herrebout W, van der Veken B et al (2006) Intermolecular association of tetrahydrofuran-2-carboxylic acid in solution: a vibrational circular dichroism study. J Phys Chem A 110:10191-10200 (Pubitemid 44412364)
87. Sander W, Gantenberg M (2005) Aggregation of acetic and propionic acid in argon matrices - a matrix isolation and computational study. Spectrochim Acta A 62:902-909 (Pubitemid 41661114)
88. Chandra AK, Parveen S, Zeegers-Huyskens T (2007) Anomeric effects in the symmetrical and asymmetrical structures of triethylamine. Blue-shifts of the C-H stretching vibrations in complexed and protonated triethylamine. J Phys Chem A 111:8884-8891 (Pubitemid 47497604)
89. Demyanov PI, Gschwind RM (2006) Formation of hydrogen bonds in complexes between dimethylcuprate(I) anion and methane, propane, or dimethyl ether. A theoretical study. Organometallics 25:5709-5723 (Pubitemid 44865652)
90. Scharge T, Emmeluth C, Häber T et al (2006) Competing hydrogen bond topologies in 2-fluoroethanol dimer. J Mol Struct 786:86-95
91. Borho N, Xu YJ (2007) Molecular recognition in 1:1 hydrogen-bonded complexes of oxirane and trans-2, 3-dimethyloxirane with ethanol: a rotational spectroscopic and ab initio study. Phys Chem Chem Phys 9:4514-4520
92. Krishnan R, Brinkley JS, Seeger R et al (1980) Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys 72:650-654
93. Tomasi J, Persico M (1994) Molecular-interactions in solution - an overview of methods based on continuous distributions of the solvent. Chem Rev 94:2027-2094 (Pubitemid 124000195)
94. Cancès E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107:3032-3041 (Pubitemid 127568923)
95. Cramer C, Truhlar D (1999) Implicit solvation models: equilibria, structure, spectra, and dynamics. Chem Rev 99:2161-2200 (Pubitemid 129585183)
96. Klamt A, Schueuermann G (1993) COSMO - a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans 2 5:799-805
97. Klamt A (1999) In: Schleyer P v R (ed) The encyclopedia of computational chemistry. Wiley, Chichester
98. Polavarapu PL (2008) Why is it important to simultaneously use more than one chiroptical spectroscopic method for determinating the structures of chiral molecules? Chirality 20: 664-672 (Pubitemid 351656170)
99. Kirk JM (1960) The mode of action of actinomycin D. Biochim Biophys Acta 42:167-169
100. Di Marco A, Gaetani OP, Scarpinato BM et al (1964) Daunomycin: a new antibiotic of the rhodomycin group. Nature 201:706-707
101. Fan E, Shi W, Lowary TL (2007) Synthesis of daunorubicin analogues containing truncated aromatic cores and unnatural monosaccharide residues. J Org Chem 72:2917-2928 (Pubitemid 46624425)
102. Corbridge DEC (2000) Phosphorus, chemistry, biochemistry and technology, 4th edn. Elsevier, Amsterdam
103. Westheimer FH (1968) Pseudo-rotation in the hydrolysis of phosphate esters. Acc Chem Res 1:70-78
104. Buchwald SL, Pliura DH, Knowla JR (1980) Stereochemical evidence for pseudorotation in the reaction of a phosphoric monoester. J Am Chem Soc 106:4916-4922
105. Knowles JR (1980) Enzyme-catalyzed phosphoryl transfer-reactions. Annu Rev Biochem 49:877-919
106. Vanool PJJM, Buck HM (1984) Trigonal bipyramidal phosphoranes as model compounds for the description of camp-catalyzed reactions. Trau Chi Pays-Bas 103:119-122
107. Holmes RR (1980) Pentacoordinated phosphorus, vol. 11. American Chemical Society, Washington, DC, p 87
108. Holmes RR (2004) Phosphoryl transfer enzymes and hypervalent phosphorus chemistry. Acc Chem Res 37:746-753
109. Holmes RR (1998) Hexacoordinate phosphorus via donor interaction. Implications regarding enzymatic reaction intermediates. Acc Chem Res 31:535-542 (Pubitemid 128473646)
110. Fu H, Li ZL, Zhao YF et al (1999) Oligomerization of N,O- bis(trimethylsilyl)-alpha-amino acids into peptides mediated by o-phenylene phosphorochloridate. J Am Chem Soc 121:291-295
111. Lahiri SD, Zhang GF, Dunaway-Mariano D et al (2003) The pentacovalent phosphorus intermediate of a phosphoryl transfer reaction. Science 299:2067-2071 (Pubitemid 36383733)
112. Leiros I, McSweeney S, Hough E (2004) The reaction mechanism of phospholipase D from Streptomyces sp strain PMF. snapshots along the reaction pathway reveal a pentacoordinate reaction intermediate and an unexpected final product. J Mol Biol 339:805-820 (Pubitemid 38686346)
113. Williams NH (2004) Models for biological phosphoryl transfer. Biochim Biophys Acta 1697:279-287 (Pubitemid 38326779)
114. Cleland WW, Hengge AC (2006) Enzymatic mechanisms of phosphate and sulfate transfer. Chem Rev 106:3252-3278 (Pubitemid 44376935)
115. Wittinghofer A (2006) Phosphoryl transfer in Ras proteins, conclusive or elusive? Trends Biochem Sci 31:20-23 (Pubitemid 43117538)
116. Catrina I, O'Brien PJ, Purcell J et al (2007) Probing the origin of the compromised catalysis of E. coli alkaline phosphatase in its promiscuous sulfatase reaction. J Am Chem Soc 129:5760-5765 (Pubitemid 46697668)
117. Fu H, Xu JH, Wang RJ et al (2003) Synthesis, crystal structure, and diastereomeric transfer of pentacoordinated phosphoranes containing valine or iso-leucine residue. Phosphorus Sulfur Silicon Relat Elem 178:1963-1971 (Pubitemid 37315387)
118. Timosheva NV, Chandrasekaran A, Holmes RR (2005) Atrane and phosphorane formation with aminotriphenols [1]. J Am Chem Soc 127:12474-12475
119. Hou JB, Tang G, Guo JN et al (2009) Stereochemistry of chiral pentacoordinate spiropho-sphoranes correlated with solid-state circular dichroism and H-1 NMR spectroscopy. Tetrahedron Asymmetry 20:1301-1307
120. 2O: a biography of water. Weidenfeld & Nicolson, London
121. Yves M (2007) The hydrogen bond and the water molecule. Elsevier, New York
122. Hobza P, Zahradnik R (1988) Intermolecular interactions between medium-sized systems - nonempirical and empirical calculations of interaction energies - successes and failures. Chem Rev 88:871-897
123. Curtiss LA, Blander M (1988) Thermodynamic properties of gas-phase hydrogen-bonded complexes. Chem Rev 88:827-841
124. Ruan CY, Lobastov VA, Vigliotti F et al (2004) Ultrafast electron crystallography of interfacial water. Science 304:80-84 (Pubitemid 38451459)
125. Wernet P, Nordlund D, Bergmann U et al (2004) The structure of the first coordination shell in liquid water. Science 304:995-999 (Pubitemid 38638094)
126. Smith JD, Cappa CD, Wilson KR et al (2004) Energetics of hydrogen bond network rearrangements in liquid water. Science 304:851-853 (Pubitemid 39446989)
127. Bukowski R, Szalewicz K, Groenenboom GC et al (2007) Predictions of the properties of water from first principles. Science 315:1249-1252 (Pubitemid 46364257)
128. 0 -methylamide: a density functional analysis of the vibrational absorption and vibrational circular dichroism spectra. Chem Phys 208:81-116
129. Jurgensen VW, Jalkanen K (2006) The VA, VCD, Raman and ROA spectra of tri-L-serine in aqueous solution. Phys Biol 3:S63-S69
130. Losada M, Tran H, Xu Y (2008) Lactic acid in solution: investigations of lactic acid self-aggregation and hydrogen bonding interactions with water and methanol using VA and VCD spectroscopy. J Chem Phys 128:014508
131. Losada M, Nguyen P, Xu Y (2008) Solvation of propylene oxide in water: vibrational circular dichroism, optical rotation, and computer simulation studies. J Phys Chem A 112:5621-5627
132. Yang GC, Xu Y (2009) Probing chiral solute-water hydrogen bonding networks by chirality transfer effects: a vibrational circular dichroism study of glycidol in water. J Chem Phys 130:164506
133. Guardia E, Marti J, Garcia-Tarres L et al (2005) A molecular dynamics simulation study of hydrogen bonding in aqueous ionic solutions. J Mol Liq 117:63-67 (Pubitemid 40205979)
134. Kongsted J, Mennucci B (2007) How to model solvent effects on molecular properties using quantum chemistry? Insights from polarizable discrete or continuum solvation models. J Phys Chem A 111:9890-9900 (Pubitemid 47598297)
135. Mukhopadhyay P, Zuber G, Goldsmith MR et al (2006) Solvent effect on optical rotation: a case study of methyloxirane in water. Chemphyschem 7:2483-2486
136. Malaspina T, Fileti EE, Rivelino R (2007) Structure and UV-vis spectrum of c60 fullerene in ethanol: a sequential molecular dynamics/quantum mechanics study. J Phys Chem B 111:11935-11939 (Pubitemid 350068909)
137. Case DA, Darden TA, Cheatham TE et al (2006) AMBER 9. University of California, San Francisco, CA
138. Jorgensen WL, Jenson C (1998) Temperature dependence of TIP3P, SPC, and TIP4P water from NPT Monte Carlo simulations: seeking temperatures of maximum density. J Comput Chem 19:1179-1186 (Pubitemid 128604734)
139. Jorgensen WL, Chandrasekhar J, Madura JD et al (1983) Comparison of simple potential functions for simulating liquid water. J Chem Phys 79:926-935
140. Yang GC, Xu Y (2008) The effects of self-aggregation on the vibrational circular dichroism and optical rotation measurements of glycidol. Phys Chem Chem Phys 10:6787-6795
141. Cj B, Drake AF, Kuroda R et al (1980) Vibrational electronic interaction in the infrared circular-dichroism spectra of transition-metal complexes. Chem Phys Lett 70:8-10
142. He YN, Cao XL, Nafie LA et al (2001) Ab initio VCD calculation of a transition-metal containing molecule and a new intensity enhancement mechanism for VCD. J Am Chem Soc 123:11320-11321 (Pubitemid 33065381)
143. Fano U (1961) Effects of configuration interaction on intensities and phase shifts. Phys Rev 124:1866-1878
144. Nafie LA (2004) Theory of vibrational circular dichroism and infrared absorption: extension to molecules with low-lying excited electronic states. J Phys Chem A 108:7222-7231
145. Sato H, Taniguchi T, Monde K, Nishimura S-I, Yamagishi A (2006) Dramatic effects of d-electron configurations on vibrational circular dichroism spectra of tris(acetylacetonato) metal(III). Chem Lett 35:364-365 (Pubitemid 44031205)
146. Sato H, Taniguchi K, Nakahashi A, Monde K, Yamagishi A (2007) Effects of central metal ions on vibrational circular dichroism spectra of tris-(â-diketonato)metal(III) complexes. Inorg Chem 46:6755-6766
147. Nicu VP, Autschbach J, Baerends EJ (2009) Enhancement of IR and VCD intensities due to charge transfer. Phys Chem Chem Phys 11:1526-1538
148. Young DA, Freedman TB, Lipp ED et al (1986) Vibrational circular-dichroism in transition-metal complexes. 2. Ion association, ring conformation, and ring currents of ethylenediamine ligands. J Am Chem Soc 108:7255-7263
149. Freedman TB, Cao XL, Young DA et al (2002) Density functional theory calculations of vibrational circular dichroism in transition metal complexes: Identification of solution conformations and mode of chloride ion association for (+)-tris(ethylenediaminato)cobalt (III). J Phys Chem A 106:3560-3565 (Pubitemid 35289822)
150. Daniel MC, Astruc D (2004) Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotech-nology. Chem Rev 104:293-346
151. Humblot V, Haq S, Muryn C et al (2002) From local adsorption stresses to chiral surfaces: (R,R)-tartaric acid on Ni(110). J Am Chem Soc 124:503-510 (Pubitemid 34086932)
152. Hofer WA, Humblot V, Raval R (2004) Conveying chirality onto the electronic structure of achiral metals: (R,R)-tartaric acid on nickel. Surf Sci 554:141-149
153. López-Lozano X, Pérez LA, Garzón IL (2006) Enantiospecific adsorption of chiral molecules on chiral gold clusters. Phys Rev Lett 97:233401
154. Gautier C, Bürgi T (2005) Vibrational circular dichroism of N-acetyl-L-cysteine protected gold nanoparticles. Chem Commun 5393-5395 (Pubitemid 41689367)
155. Gautier C, Bürgi T (2006) Chiral N-isobutyryl-cysteine protected gold nanoparticles: preparation, size selection, and optical activity in the UV-vis and infrared. J Am Chem Soc 128:11079-11087 (Pubitemid 44300117)
156. Gautier C, Bürgi T (2010) Vibrational circular dichroism of adsorbed molecules: binas on gold nanoparticles. J Phys Chem C. doi:10.1021/jp910800m
157. 0-dithiol-stabilized gold clusters: size separation and optical activity in the UV-vis. Chirality 20:486-493 (Pubitemid 351303989)
158. Bürgi T, Bieri M (2004) Time-resolved in situ ATR Spectroscopy of 2-propanol oxidation over Pd/Al2O3: evidence for 2-propoxide intermediate. J Phys Chem B 108:13364-13369
159. Neurock M (1999) First-principles analysis of the hydrogenation of carbon monoxide over palladium. Top Catal 9:135-152
160. Schlosser DW, Devlin F, Jalkanen K et al (1982) Vibrational circular-dichroism of matrix-isolated molecules. Chem Phys Lett 88:286-291
161. Polavarapu PL, Hess BA, Schaad LJ (1985) Vibrational-spectra of epoxypropane. J Phys Chem 82:1705-1710
162. Lowe MA, Alper JS, Kawiecki R et al (1986) Scaled abinitio force-fields for ethylene-oxide and propylene-oxide. J Phys Chem 90:41-50
163. Tarczay G, Magyarfalvi G, Vass E (2006) Towards the determination of the absolute configuration of complex molecular systems: matrix isolation vibrational circular dichroism study of (R)-2-amino-1-propanol. Angew Chem Int Ed 45:1775-1777 (Pubitemid 44105253)
164. Qu X, Citra M, Ragunathan N et al (1993) Proceedings of the 9th International Conference on Fourier Transform Spectroscopy (SPIE vol. 2089, p 142
165. Fausto R, Cacela C, Duarte ML (2000) Vibrational analysis and structural implications of H-bonding in isolated and aggregated 2-amino-1-propanol: a study by MI-IR and Raman spectroscopy and molecular orbital calculations. J Mol Struct 550-551:365-388
166. Pohl G, Perczel A, Vass E et al (2007) A matrix isolation study on Ac-Gly-NHMe and Ac-L-Ala-NHMe, the simplest chiral and achiral building blocks of peptides and proteins. Phys Chem Chem Phys 9:4698-4708
167. Pohl G, Perczel A, Vass E et al (2008) A matrix isolation study on Ac-L-Pro-NH2: a frequent structural element of beta- and gamma-turns of peptides and proteins. Tetrahedron 64:2126-2133
168. Tarczay G, Gobi S, Vass E et al (2009) Model peptide-water complexes in Ar matrix: complexation induced conformation change and chirality transfer. Vib Spectrosc 50:21-28
169. Sadlej J, Dobrowolski JC, Rode JE (2010) VCD spectroscopy as a novel probe for chirality transfer in molecular interactions. Chem Soc Rev 39:1478-1488
170. Muller T, Wiberg KB, Vaccaro PH (2000) Cavity ring-down polarimetry (CRDP): a new scheme for probing circular birefringence and circular dichroism in the gas phase. J Phys Chem 104:5959-5968
171. Muller T, Wiberg KB, Vaccaro PH et al (2002) Cavity ring-down polarimetry (CRDP): theoretical and experimental characterization. J Opt Soc Am B 19:125-141
172. Bonmarin M, Helbing J (2008) A picosecond time-resolved vibrational circular dichroism spectrometer. Optics Lett 33:2086-2088
173. Xie X, Simon JD (1990) Picosecond time-resolved circular-dichroism study of protein relaxation in myoglobin following photodissociation of CO. J Am Chem Soc 112: 7802-7803 (Pubitemid 20355859)
174. Xie X, Simon JD (1990) Picosecond circular-dichroism spectroscopy - a Jones matrix analysis. J Opt Soc Am B 7:1673-1684
175. Xie X, Simon JD (1989) Picosecond time-resolved circular-dichroism spectroscopy - experimental details and applications. Rev Sci Instrum 60:2614-2627
176. Rhee H, Ha JH, Jeon SJ et al (2008) Femtosecond spectral interferometry of optical activity: theory. J Chem Phys 129:094507
177. Rhee H, June YG, Lee JS et al (2008) Femtosecond characterization of vibrational optical activity of chiral molecules. Nature 458:310-313
178. Rhee H, JuneYG KZH et al (2009) Phase sensitive detection of vibrational optical activity free-induction-decay: vibrational CD and ORD. J Opt Soc Am B 26:1008-1017
179. Lepetit L, Cheriaux G, Joffre M (1995) Linear techniques of phase measurement by femtosecond spectral interferometry for applications in spectroscopy. J Opt Soc Am B 12:2467-2474 (Pubitemid 126007666)
180. Fittinghoff DN, Bowie JL, Sweetser JN et al (1996) Measurement of the intensity and phase of ultraweak, ultrashort laser pulses. Opt Lett 21:884-886 (Pubitemid 126579409)
181. Su Z, Wen Q, Xu Y (2006) Conformational stability of the propylene oxide-water adduct: direct spectroscopic detection of O-H. . .O hydrogen bonded conformers. J Am Chem Soc 128:6755-6760
182. 2 cluster in the gas phase. Angew Chem Int Ed 46:6163-6166 (Pubitemid 47290977)
183. Zehnacker A, Suhm MA (2008) Chirality recognition between neutral molecules in the gas phase. Angew Chem Int Ed 47:6970-6992