Quantitative Analyses of Molecular Surface Electrostatic Potentials in Relation to Hydrogen Bonding and Co-Crystallization

Crystal Growth and Design

Volumn 15, Issue 8, 2015, Pages 3767-3774

  Politzer, Peter ^a,b   Murray, Jane S ^a,b  

^a University of New Orleans   (United States)

^b CleVeTheoComp LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATICS; IONS;

CO-CRYSTALLIZATIONS; COCRYSTALLIZATION; ELECTROSTATIC POTENTIALS; MOLECULAR SURFACE ELECTROSTATIC POTENTIALS; MOLECULAR SURFACES; NEGATIVE VALUES; NON-COVALENT INTERACTION; SURFACE ELECTROSTATIC POTENTIAL;

HYDROGEN BONDS;

EID: 84938633712     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/acs.cgd.5b00419     Document Type: Article

References (85)

1. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126 10.1021/ar00172a005
2. Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610 10.1021/j100165a007
3. Donohue, J. J. Phys. Chem. 1952, 56, 502-510 10.1021/j150496a023
4. Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095-1096 10.1021/ja00368a031
5. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887 10.1021/jo00165a018
6. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 699-711 10.1039/p29890000699
7. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521-529 10.1039/p29900000521
8. Taft, R. W.; Murray, J. S. In Quantitative Treatments of Solute/Solvent Interactions, Politzer, P.; Murray, J. S., Eds.; Elsevier: Amsterdam, 1994; pp 55-82.
9. Abraham, M. H. In Quantitative Treatments of Solute/Solvent Interactions, Politzer, P.; Murray, J. S., Eds.; Elsevier: Amsterdam, 1994; pp 83-134.
10. Murray, J. S.; Ranganathan, S.; Politzer, P. J. Org. Chem. 1991, 56, 3734-3737 10.1021/jo00011a060
11. Murray, J. S.; Politzer, P. J. Org. Chem. 1991, 56, 6715-6717 10.1021/jo00023a045
12. Hagelin, H.; Murray, J. S.; Brinck, T.; Berthelot, M.; Politzer, P. Can. J. Chem. 1995, 73, 483-488 10.1139/v95-063
13. Stewart, R. F. Chem. Phys. Lett. 1979, 65, 335-342 10.1016/0009-2614(79)87077-3
14. Politzer, P.; Truhlar, D. G., Eds. Chemical Applications of Atomic and Molecular Electrostatic Potentials; Plenum: New York, 1981.
15. Klein, C. L.; Stevens, E. D. In Structure and Reactivity, Liebman, J. F.; Greenberg, A., Eds.; VCH: New York, 1988; Chapter 2, pp 25-64.
16. Bader, R. F. W.; Carroll, M. T.; Cheeseman, J. R.; Chang, C. J. Am. Chem. Soc. 1987, 109, 7968-7979 10.1021/ja00260a006
17. Murray, J. S.; Politzer, P. Croat. Chim. Acta 2009, 82, 267-275
18. Bulat, F. A.; Toro-Labbé, A.; Brinck, T.; Murray, J. S.; Politzer, P. J. Mol. Model. 2010, 16, 1679-1691 10.1007/s00894-010-0692-x
19. Politzer, P.; Murray, J. S.; Clark, T. Topics Curr. Chem. 2015, 358, 19-42 10.1007/128-2014-568
20. Politzer, P.; Murray, J. S.; Clark, T. J. Mol. Model. 2015, 21 (52) 1-10
21. Schrödinger, E. Ann. Phys. 1926, 80, 437-490 10.1002/andp.19263851302
22. Güttinger, P. Eur. Phys. J. A 1932, 73, 169-184 10.1007/BF01351211
23. Hellmann, H. Eur. Phys. J. A 1933, 85, 180-190 10.1007/BF01342053
24. Pauli, W. Handbuch der Physik, 24, Springer: Berlin, 1933; p 162.
25. Feynman, R. P. Phys. Rev. 1939, 56, 340-343 10.1103/PhysRev.56.340
26. Levine, I. N. Quantum Chemistry, 5 th ed.; Prentice-Hall: Upper Saddle River, NJ, 2000.
27. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960.
28. Kollman, P.; McKelvey, J.; Johansson, A.; Rothenberg, S. J. Am. Chem. Soc. 1975, 97, 955-965 10.1021/ja00838a001
29. Umeyama, H.; Morokuma, K. J. Am. Chem. Soc. 1977, 99, 1316-1332 10.1021/ja00447a007
30. Buckingham, A. D.; Fowler, P. W. Can. J. Chem. 1985, 63, 2018-2025 10.1139/v85-334
31. Lin, S.; Dykstra, C. E. Chem. Phys. 1986, 107, 343-349 10.1016/0301-0104(86)85012-1
32. Legon, A. C.; Millen, D. J. Acc. Chem. Res. 1987, 20, 39-46 10.1021/ar00133a006
33. Politzer, P.; Daiker, K. C. In The Force Concept in Chemistry; Deb, B. M.; Ed.; Van Nostrand Reinhold: New York, 1981; pp 294-387k.
34. Arunan, R.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Damenberg, J. J.; Hobza, P.; Kjaergaard, H. G.; Legon, A. C.; Mennucci, B.; Nesbitt, D. J. Pure Appl. Chem. 2011, 83, 1619-1636 10.1351/PAC-REC-10-01-02
35. Morokuma, K.; Kitaura, K. In Chemical Applications of Atomic and Molecular Electrostatic Potentials, Politzer, P.; Truhlar, D. G.; Eds.; Plenum: New York, 1981; pp 215-242.
36. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926 10.1021/cr00088a005
37. Sokalski, W. A.; Roszak, S. M. J. Mol. Struct.: THEOCHEM 1991, 234, 387-400 10.1016/0166-1280(91)89025-V
38. Scheiner, S. In Reviews in Computational Chemistry, Lipkowitz, K. B.; Boyd, D. B.; Eds.; VCH: Weinheim, Germany, 1991; Vol. 2, pp 165-218.
39. Stone, A. J.; Misquitta, A. J. Chem. Phys. Lett. 2009, 473, 201-205 10.1016/j.cplett.2009.03.073
40. Azar, R. J.; Horn, P. R.; Sundstrom, E. J.; Head-Gordon, M. J. Chem. Phys. 2013, 138, 84102-84115 10.1063/1.4792434
41. Clark, T.; Politzer, P.; Murray, J. S. WIREs Comp. Mol. Sci. 2015, 5, 169 10.1002/wcms.1210
42. Wang, W.; Wang, N. B.; Zheng, W.; Tian, A. J. Phys. Chem. A 2004, 108, 1799-1805 10.1021/jp036769q
43. Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699-704 10.1007/s00894-008-0307-y
44. Hermansson, K. J. Phys. Chem. A 2002, 106, 4695-4702 10.1021/jp0143948
45. Qian, W.; Krimm, S. J. Phys. Chem. A 2002, 106, 6628-6636 10.1021/jp020438g
46. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324 10.1002/anie.200301739
47. Aakeröy, C. B.; Epa, K.; Forbes, S.; Schultheiss, N.; Desper, J. Chem.-Eur. J. 2013, 19, 14998-15003 10.1002/chem.201301402
48. Aakeröy, C. B.; Wijethunga, T. K.; Desper, J. New J. Chem. 2015, 39, 822-828 10.1039/C4NJ01324G
49. Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 1992, 44 (S19) 57-64 10.1002/qua.560440709
50. Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 1993, 48, 73-88 10.1002/qua.560480202
51. Murray, J. S.; Lane, P.; Clark, T.; Politzer, P. J. Mol. Model. 2007, 13, 1033-1038 10.1007/s00894-007-0225-4
52. Murray, J. S.; Lane, P.; Politzer, P. Int. J. Quantum Chem. 2007, 107, 2286-2292 10.1002/qua.21352
53. Murray, J. S.; Lane, P.; Politzer, P. J. Mol. Model. 2009, 15, 723-729 10.1007/s00894-008-0386-9
54. Politzer, P.; Murray, J. S. ChemPhysChem 2013, 14, 278-294 10.1002/cphc.201200799
55. Politzer, P.; Murray, J. S.; Clark, T. Phys. Chem. Chem. Phys. 2013, 15, 11178-11189 10.1039/c3cp00054k
56. Legon, A. C. Struct. Bonding (Berlin) 2008, 126, 17-64
57. Shields, Z. P.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 2010, 110, 2823-2832 10.1002/qua.22787
58. Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 14, 1504-1518 10.1002/jcc.540141213
59. Price, S. L.; Stone, A. J. J. Chem. Phys. 1987, 86, 2859-2868 10.1063/1.452037
60. Stone, A. J.; Price, S. L. J. Phys. Chem. 1988, 92, 3325-3335 10.1021/j100323a006
61. Price, S. L. J. Chem. Soc., Faraday Trans. 1996, 92, 2997-3008 10.1039/ft9969202997
62. Auffinger, P.; Hays, F. A.; Westhof, E.; Shing Ho, P. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16789-16794 10.1073/pnas.0407607101
63. Politzer, P.; Murray, J. S.; Concha, M. C. J. Mol. Model. 2008, 14, 659-665 10.1007/s00894-008-0280-5
64. Kolář, M.; Hobza, P. J. Chem. Theory Comput. 2012, 8, 1325-1333 10.1021/ct2008389
65. Carter, M.; Rappé, A. K.; Shing, H. P. J. Chem. Theory Comput. 2012, 8, 2461-2473 10.1021/ct3001969
66. Jorgensen, W. L.; Schyman, P. J. Chem. Theory Comput. 2012, 8, 3895-3901 10.1021/ct300180w
67. Panunto, T. W.; Urbánczyk-Lipkowska, Z.; Johnson, R.; Etter, M. C. J. Am. Chem. Soc. 1987, 109, 7786-7797 10.1021/ja00259a030
68. Etter, M. C.; Urbánczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415-8426 10.1021/ja00179a028
69. Murray, J. S.; Grice, M. E.; Politzer, P.; Etter, M. C. Mol. Eng. 1991, 1, 75-87 10.1007/BF00625739
70. Riley, K. E.; Murray, J. S.; Politzer, P.; Concha, M. C.; Hobza, P. J. Chem. Theory Comput. 2009, 5, 155-163 10.1021/ct8004134
71. Etter, M. C.; Frankenbach, G. M. Chem. Mater. 1989, 1, 10-12 10.1021/cm00001a005
72. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395 10.1021/ar0400995
73. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127 10.1002/anie.200800128
74. Legon, A. C. Phys. Chem. Chem. Phys. 2010, 12, 7736-7747 10.1039/c002129f
75. Politzer, P.; Murray, J. S. Adv. Quantum Chem. 2014, 69, 1-30
76. Bolton, O.; Matzger, A. J. Angew. Chem., Int. Ed. 2011, 50, 8960-8963 10.1002/anie.201104164
77. Bolton, O.; Simke, L. R.; Pagoria, P. F.; Matzger, A. J. Cryst. Growth Des. 2012, 12, 4311-4314 10.1021/cg3010882
78. Landenberger, K. B.; Matzger, A. J. Cryst. Growth Des. 2012, 12, 3603-3609 10.1021/cg3004245
79. Li, H.; Shu, Y.; Gao, S.; Chen, L.; Ma, Q.; Ju, X. J. Mol. Model. 2013, 19, 4909-4917 10.1007/s00894-013-1988-4
80. Grecu, T.; Hunter, C. A.; Gardner, E. J.; McCabe, J. F. Cryst. Growth Des. 2014, 14, 165-171
81. Murray, J. S.; Concha, M. C.; Politzer, P. Mol. Phys. 2009, 107, 89-97 and references cited. 10.1080/00268970902744375
82. Politzer, P.; Murray, J. S. In Green Energetic Materials, Brinck, T.; Ed., Wiley: Chichester, UK, 2014; pp 45-62, and references cited.
83. Meyer, R.; Köhler, J.; Homburg, A. Explosives, 6 th ed.; Wiley-VCH: Weinheim, Germany, 2007.
84. Politzer, P.; Abrahmsen, L.; Sjoberg, P. J. Am. Chem. Soc. 1984, 106, 855-860 10.1021/ja00316a005
85. Politzer, P.; Laurence, P. R.; Abrahmsen, L.; Zilles, B. A.; Sjoberg, P. Chem. Phys. Lett. 1984, 111, 75-78 10.1016/0009-2614(84)80439-X