Hydrogen bonding strength - Measures based on geometric and topological parameters

Journal of Physical Organic Chemistry

Volumn 17, Issue 1, 2004, Pages 18-31

  Grabowski, Sławomir Janusz ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Ab initio calculations; Bader theory; Bond critical points; Hydrogen bonding; Intermolecular H bonds; Intramolecular H bonds; Measures of H bond strength; Ring critical points

Indexed keywords

ALDEHYDES; BINDING ENERGY; CARRIER CONCENTRATION; CRYSTAL STRUCTURE; CRYSTALS; DERIVATIVES; HYDROGEN BONDS; INDICATORS (CHEMICAL); NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS;

BADER THEORY; BASIS SET SUPERPOSITION ERRORS (BSSE); BOND CRITICAL POINTS; INTERMOLECULAR HYDROGEN BONDS; RING CRITICAL POINTS;

BOND STRENGTH (CHEMICAL);

EID: 0346055206     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.685     Document Type: Review

References (116)

1. Jeffrey GA, Saenger W. Hydrogen Bonding in Biological Structures. Springer: Berlin, 1991.
2. Desiraju GR. Crystal Engineering - The Design of Organic Solids. Elsevier: Amsterdam, 1989.
3. Krygowski TM, Cyrański MK, Czarnocki Z, Häfelinger G, Katritzky AR. Tetrahedron 2000; 56: 1783-1796.
4. Krygowski TM, Cyrański MK. Chem. Rev. 2001; 101:1385-1419.
5. Jeffrey GA. An Introduction to Hydrogen Bonding. Oxford University Press: New York, 1997.
6. Desiraju GR, Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press: New York, 1999.
7. Scheiner S. Hydrogen Bonding: A Theoretical Perspective. Oxford University Press: New York, 1997.
8. Pimentel GC, McClellan AL. The Hydrogen Bond. Freeman: San Francisco, 1960.
9. Taylor R, Kennard O. J. Am. Chem. Soc. 1982; 104: 5063-5070.
10. Desiraju GR. Angew. Chem., Int. Ed. Engl. 1995; 34: 2311-2327.
11. Steiner T. Angew. Chem., Int. Ed. Engl. 2002; 41: 48-76.
12. Etter MC. Acc. Chem. Res. 1990; 23: 120-126.
13. Viswamitra MA, Radhakrishnan R, Bandekar J, Desiraju GR. J. Am. Chem. Soc. 1993; 115: 4868-4869.
14. Alkorta I, Rozas I, Elguero J. Chem. Soc. Rev. 1998; 27: 163-170, and references cited therein.
15. Gu J, Kar T, Scheiner S. J. Am. Chem. Soc. 1999; 121: 9411-9422.
16. Leiserowitz L. Acta Crystallogr., Sect. B 1976; 32: 775-802.
17. Grabowski SJ. Pol J. Chem. 1995; 69: 223-228.
18. Larson JW, McMahon TB. J. Am. Chem. Soc. 1983; 103: 2944-2950.
19. Latajka Z, Bouteller Y, Scheiner S. Chem. Phys. Lett. 1995; 234: 159-164.
20. Gilli G, Bellucci F, Ferretti V, Bertolasi V. J. Am. Chem. Soc. 1989; 111: 1023-1028.
21. Gilli P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 1994; 116: 909-915.
22. Madsen GKH, Iversen BB, Larsen FK, Kapon M, Reisner GM, Herbstein FH. J. Am. Chem. Soc. 1998; 120: 10040-10045.
23. González L, Mó O, Yáñez M, Elguero J. J. Chem. Phys. 1998; 109: 2685-2693.
24. Tokhadze KG, Denisov GS, Wierzejewska M, Drozd M. J. Mol. Struct. 1997; 404: 55-62.
25. Kaplan IG. Theory of Molecular Interactions. Studies in Physical and Theoretical Chemistry, vol. 42. Elsevier: Amsterdam, 1986.
26. Platts JA, Howard ST, Woźniak K. Chem. Commun. 1996; 63-64.
27. Gilli G, Gilli P. J. Mol. Struct. 2000; 552: 1-15.
28. Hibbert F, Emsley J. Adv. Phys. Org. Chem. 1990; 26: 255.
29. Garcia-Viloca M, Gelabert R, González-Lafont A, Moreno M, Lluch JM. J. Phys. Chem. A 1997; 101: 8727-8733.
30. Berglund B, Vaughan RW. J. Chem. Phys. 1980; 73: 2037-2043.
31. Gerald R, Bernhard T, Haeberlen U, Rendell J, Opella S. J. Am. Chem. Soc. 1993; 115: 777-782.
32. Kaliaperumal L, Sears REJ, Ni QW, Furst JE. J. Chem. Phys. 1989; 91: 7387-7391.
33. Scheiner S, Gu Y, Kar T. J. Mol. Struct. (Theochem) 2000; 500: 441-452.
34. Scheiner S, Grabowski SJ, Kar T. J. Phys. Chem. A 2001; 105: 10607-10612.
35. Scheiner S, Grabowski SJ. J. Mol. Struct. 2002; 615: 209-218.
36. Bader RFW. Atoms in Molecules: A Quantum Theory. Oxford University Press: New York, 1990.
37. Parr RG, Yang W. Density-Functional Theory of Atoms and Molecules. Oxford University Press: New York, 1989.
38. Alcamí M, Mó O, Yáñez M. Mass Spectrom. Rev. 2001; 20: 195-245.
39. González L, Mó O, Yáñez. J. Org. Chem. 1999; 64: 2314-2321.
40. Lutz HD. J. Mol. Struct. 2003; 646: 227-236.
41. Ichikawa M. Acta Crystallogr., Sect. B 1978; 34: 2074-2080.
42. Ichikawa M. J. Mol. Struct. 2000; 552: 63-70.
43. Grabowski SJ. Tetrahedron 1998; 54: 10153-10160.
44. Grabowski SJ. J. Phys. Chem. A 2001; 105: 10739-10746.
45. Boys SF, Bernardi F. Mol. Phys. 1970; 19: 553.
46. van Duijneveldt FB, van Duijneveldt-van de Rijdt JGCM, van Lenthe JH. Chem. Rev. 1994; 94: 1873-1885.
47. Simon S, Bertran J, Sodupe M. J. Phys. Chem. A 2001; 105: 4359-4364.
48. Grabowski SJ. J. Mol. Struct. 2002; 615: 239-245.
49. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson GB, Robb MA, Cheeseman JR, Keith TA, Petersson GA, Montgomery JA, Raghavachari K, Al.-Laham MA, Zakrzewski VG, Ortiz JV, Foresman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replogle ES, Gomperts R, Martin LR, Fox DJ, Binkley JS, Defrees DJ, Steward JJ, Head-Gordon M, Gonzalez G, Pople JA. Gaussian 94. Gaussian: Pittsburgh, PA, 1995.
50. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin LR, Fox DJ, Keith T, Al.-Laham MA, Peng CY, Nanayakkara A, Gonzalez G, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.6. Gaussian: Pittsburgh, PA, 1998.
51. Grabowski SJ. Chem. Phys. Lett. 2001; 338: 361-366.
52. 2M, Grenoble, France December 1998; AIP (American Institute of Physics) College Park, MD; Conference Proceedings 479, Johnson MR, Kearley GJ, Büttner HG (eds). American Institute of Physics, 1999.
53. Allen FH, Davies JE, Galloy JE, Johnson JJ, Kennard O, Macrave CF, Mitchel EM, Smith JM, Watson DG. J. Chem. Inf. Comput. Sci. 1991; 31: 187.
54. Steiner T. Chem. Soc., Perkin Trans. 2 1996; 1315-1319.
55. Allerhand A, Schleyer R. J. Am. Chem. Soc. 1963; 85: 1715.
56. McWeeny R. Coulson's Valence. Oxford University Press: London, 1979.
57. Pauling L. J. Am. Chem. Soc. 1947; 69: 542.
58. Cieplak AS. In Structure Correlation, Bürgi H-B, Dunitz JD (eds). VCH: Weinheim, 1994, and references cited therein.
59. Bürgi HB, Shklover V. In Structure Correlation, Bürgi H-B, Dunitz JD (eds). VCH: Weinheim, 1994, and references cited therein.
60. Brown ID, Shannon RD. Acta Crystallogr., Sect. A 1972; 29: 266-282.
61. Brown ID. Acta Crystallogr., Sect. B 1992; 48: 553-572, and references cited therein.
62. Grabowski SJ. Croat. Chem. Acta 1988; 61: 815-819.
63. Grabowski SJ. J. Mol. Struct. 2000; 552: 153-157.
64. Steiner T. J. Phys. Chem. 1998; 102: 7041-7052.
65. Grabowski SJ. Chem. Phys. Lett. 1999; 312: 542-547.
66. Grabowski SJ. J. Phys. Chem. A 2000; 104: 5551-5557.
67. Richardson TB, deGala S, Crabtree RH, Siegbahn PEM. J. Am. Chem. Soc. 1995; 117: 12875.
68. Crabtree RH, Siegbahn PEM, Eisenstein O, Rheingold AL, Koetzle TF. Acc. Chem. Res. 1996; 29: 348-354.
69. Epstein LM, Shubina ES. Coord. Chem. Rev. 2002; 231: 165-181, and references cited therein.
70. Liu Q, Huffman R. J. Am. Chem. Soc. 1995; 117: 10108.
71. Alkorta I, Elguero J, Foces-Foces C. Chem. Commun. 1996; 1633-1634.
72. Orlowa G, Scheiner S, Kar T. J. Phys. Chem. A 1999; 103: 514-520.
73. Grabowski SJ, Pogorzelska M. J. Mol. Struct. 2001; 559: 201-207.
74. Krygowski TM, Grabowski SJ, Konarski J. Tetrahedron 1998; 54: 11311-11316.
75. Palusiak M, Grabowski SJ. J. Mol. Struct. 2002; 642: 97-104.
76. Dunitz JD. X-Ray Analysis and the Structure of Organic Molecules. Cornell University Press: Ithaca, NY, 1979; 341-363.
77. Bürgi HB, Dunitz JD. J. Am. Chem. Soc. 1987; 109: 2924-2926.
78. Bürgi HB. Angew. Chem., Int. Ed. Engl. 1975; 14: 460-473.
79. Grabowski SJ, Krygowski TM. Chem. Phys. Lett. 1999; 305: 247-250.
80. Grabowski SJ, Krygowski TM, Sţepień B. J. Phys. Org. Chem. 2000; 13: 740-744.
81. Benedict H, Limbach H-H, Wehlan M, Fehlhammer W-P, Golubev NS, Janoschek R. J. Am. Chem. Soc. 1998; 120: 2939-2950.
82. Smirnov SN, Benedict H, Golubev NS, Denisov GS, Kreevoy MM, Schowen RL, Limbach H-H. Can. J. Chem. 1999; 77: 943-949.
83. Majerz I, Malarski Z, Sobczyk L. Chem. Phys. Lett. 1997; 274: 361-364.
84. Sobczyk L. Ber. Bunsenges. Phys. Chem. 1998; 102: 377-383.
85. Hamilton WC, Ibers JA. Hydrogen Bonding in Solids. Benjamin: New York, 1968.
86. Grabowski SJ, Krygowski TM. Tetrahedron 1998; 54: 5683-5694.
87. Lippincott ER, Schroeder R. J. Chem. Phys. 1955; 23: 1099-1106.
88. Dziembowska T, Szczodrowska B, Krygowski TM, Grabowski SJ. J. Phys. Org. Chem. 1994; 7: 142-146.
89. Koch U, Popelier PLA. J. Phys. Chem. A 1995; 99: 9747-9754.
90. Popelier P. Atoms in Molecules. An Introduction. Prentice-Hall: Englewood Cliffs, NJ, 2000.
91. Popelier PLA. J. Phys. Chem. A 1998; 102: 1873-1878.
92. Popelier PLA, Logothetis G. J. Organomet. Chem. 1998; 555: 101-111.
93. Mó O, Yánez M, Elguero J. J. Chem. Phys. 1992; 97:6628-6638.
94. Mó O, Yánez M, Elguero J. J. Mol. Struct. (Theochem) 1994; 314: 73-81.
95. Koch W, Frenking G, Gauss J, Cremer D, Collins JR. J. Am. Chem. Soc. 1987; 109: 5917-5934.
96. Rozas I, Alkorta I, Elguero J. J. Am. Chem. Soc. 2000; 122: 11154-11161.
97. Abramov YA. Acta Crystallogr., Sect. A 1997; 53: 264-272.
98. Espinosa E, Molins E, Lecomte C. Chem. Phys. Lett. 1998; 285: 170-173.
99. Mallinson PR, Woźniak K, Smith GT and McCormack KL. J. Am. Chem. Soc. 1997; 119: 11502-11509.
100. Espinosa E, Alkorta I, Rozas I, Elguero J, Molins E. Chem. Phys. Lett. 2001; 336: 457-461.
101. Wojtulewski S, Grabowski SJ. J. Mol. Struct (Theochem) 2003; 621: 285-291.
102. Hobza P, Havlas Z. Chem. Rev. 2000; 100: 4253-4264, and references cited therein.
103. Muchall HM. J. Phys. Chem. A 2001; 105: 632-636.
104. Gordon MS, Jensen JH. Acc. Chem. Res. 1996; 29: 536-543.
105. Hehre WJ, Radom L, Schleyer PvR, Pople JA. Ab Initio Molecular Orbital Theory. Wiley: New York, 1986.
106. Rozas I, Alkorta I, Elguero J. J. Phys. Chem. A 2001; 105: 10462-10467.
107. Grabowski SJ. J. Mol. Struct. 2001; 563: 137-143.
108. Grabowski SJ. Monatsh. Chem. 2002; 133: 1373-1380.
109. Craw JS, Bacskay J. J. Chem. Soc. Faraday Trans. 1992; 88: 2315-2321.
110. Buemi G, Zuccarello F. J. Mol. Struct. (Theochem) 2002; 581: 71-85.
111. Bertolasi V, Gilli P, Ferretti V, Gilli G. Acta Crystallogr., Sect. B 1994; 50: 617-625.
112. Rybarczyk-Pirek AJ, Grabowski SJ, Małecka M, Nawrot-Modranka J. J. Phys. Chem. A 2002; 106: 11956-11962.
113. Grabowski SJ. In Horizons in H-bond Research, Proceeding of the Conference, Torino, September 2001.
114. Überla K. Faktorenanalyse. Springer: Berlin, 1977.
115. Malinowski ER, Howery DG. Factor Analysis in Chemistry. Wiley-Interscience: New York, 1980.
116. Fawcett WR, Krygowski TM. Can. J. Chem. 1976; 54: 3283-3292.