Novel point charge models: Reliable instruments for molecular electrostatics

Journal of Physical Organic Chemistry

Volumn 14, Issue 6, 2001, Pages 355-369

  Oliferenko, Alexander A ^a   Palyulin, Vladimir A ^a   Pisarev, Sergei A ^a   Neiman, Alexei V ^a   Zefirov, Nikolai S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Atomic charges; Electronegativity equilibration; Molecular electrostatics; Predictions of molecular properties; Topological models of chemical structures

Indexed keywords

EID: 0035368644     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.378     Document Type: Article

References (86)

1. Bachrach SM. In Reviews in Computational Chemistry, Lipkowitz KB, Boyd DB (eds). VCH: New York, 1993; vol. 5, 171-227.
2. Wiberg K, Rablen P. J. Comput. Chem. 1993; 14: 1504-1518.
3. (a) Cramer C, Truhlar D. Theor. Chim. Acta 1997; 98: 206-211;
4. (b) Li J, Zhu T, Cramer CJ, Truhlar DG. J. Phys. Chem. A 1998; 102: 1820-1831.
5. Naray-Szabo G, Ferenczy G. Chem. Rev. 1995; 95: 829-847.
6. Mulliken RS. J. Chem. Phys. 1955; 23: 1833-1840.
7. Lowdin PO. J. Chem. Phys. 1953; 21: 374.
8. Edgecombe KE, Boyd RJ. J. Chem. Soc. 1987; 1307-1315.
9. Fliszar S. Lecture Notes in Chemistry. Springer: Berlin, 1994; vol. 63.
10. Reed A, Weinstock R, Weinhold F. J. Chem. Phys. 1985; 83: 735-746.
11. (a) Bader RFW. Atoms in Molecules: a Quantum Theory. Clarendon Press: Oxford, 1990;
12. (b) Bader RFW. Johnson S, Tang TH, Popelier P. J. Phys. Chem. A 1996; 100: 15398-15415.
13. (a) Chirlian LE, Francl MM. J. Comput. Chem. 1987; 8: 894-905;
14. (b) Breneman CM, Wiberg KB. J. Comput. Chem. 1990; 11: 361-373.
15. (a) King WT, Mast GB, Blanchette PP. J. Chem. Phys. 1972; 56: 4440-4446;
16. (b) Cioslowski J. J. Am. Chem. Soc. 1989; 111: 8333-8336..
17. Hehre WJ, Radom L, Schleyer v. RP, Pople JA. Ab initio Molecular Orbital Theory. Wiley: New York, 1986.
18. Politzer P, Mulliken RS. J. Chem. Phys. 1971; 55: 5135-5136.
19. Mortier WJ, Van Genechten K, Gasteiger J. J. Am. Chem. Soc. 1985; 107: 829-835.
20. (a) Gimarc BM, Ott JJ. J. Am. Chem. Soc. 1983; 108: 4298-4303;
21. (b) Bonchev D, Kier L. J. Math. Chem. 1992; 9: 75-85;
22. (c) Galvez J, Garcia R, Salabert MT, Soler R. J. Chem. Inf. Comput. Sci. 1994; 34: 520-525.
23. Sanderson RT. J. Am. Chem. Soc. 1983; 105: 2259-2261.
24. Huheey JE. J. Phys. Chem. 1965; 69: 3284-3291.
25. Jolly WL, Perry WB. Inorg. Chem. 1974; 13: 2686-2692
26. Baumer L, Sala G, Sello G. Tetrahedron Comput. Method 1989; 2: 37-46.
27. (a) Gasteiger J, Marsili M. Tetrahedron 1980; 36: 3219-3228;
28. (b) Gasteiger J, Marsili M. Org. Magn. Reson. 1981; 15: 353-360;
29. (c) Hutchings MG, Gasteiger J. Tetrahedron Lett. 1983; 24: 2541-2544;
30. (d) Guillen MD, Gasteiger J. Tetrahedron 1983; 39: 1331-1335;
31. (e) Marsili M, Gasteiger J. Croat. Chem. Acta 1980; 53: 601-614.
32. Mullay J. J. Am. Chem. Soc. 1986; 108: 1770-1775.
33. (a) Kirpichenok MA, Zefirov NS. Russ. J. Org. Chem. 1987; 23: 673-690, 690-701;
34. (b) Zefirov NS, Kirpichenok MA, Izmailov FF, Trofimov MI. Dokl. Akad. Nauk SSSR 1987; 296: 883-887.
35. (a) Smith R, Ree T, Magee J, Eyring H. J. Am. Chem. Soc. 1951; 73: 2263-2268;
36. (b) Abraham R, Griffiths L, Loftus P. J. Comput. Chem. 1982; 3: 407-416;
37. (c) Fetisov VI, Kolesova VA, Kotov AV, Lisyanskii II, Chimishkyan AL, Martynov IV. Dokl. Akad. Nauk 1998; 358: 210-214.
38. Del Re G. J. Chem. Soc. 1958; 4031-4040.
39. Mortier WJ, Ghosh SK, Shankar S. J. Am. Chem. Soc. 1986; 108: 4315-4320.
40. Pauling L. The Nature of the Chemical Bond. Cornell University Press: Ithaca NY, 1960.
41. Balaban AT. J. Mol. Struct. (THEOCHEM) 1985; 21: 117-142.
42. (a) Katrizky AR, Sild S, Karelson M. J. Chem. Inf. Comput. Sci. 1998; 38: 1171-1176;
43. (b) Trofimov MI, Smolenskii EA. Russ. Chem. Bull. 2000; 401-406.
44. (a) Hinze J, Jaffe H. J. Am. Chem. Soc. 1962; 84: 540-546;
45. (b) Hinze J, Whitehead M, Jaffe H. J. Am. Chem. Soc. 1963; 85: 148-154.
46. PETRA. http://www2.ccc.uni-erlangen.de/software/petra/index. html
47. SYBYL 6.6.1, Tripos: St Louis, MO, 1999.
48. Palyulin VA, Radchenko EV, Zefirov NS. J. Chem. Inf. Comput. Sci. 2000; 40: 659-667.
49. Parr RG, Yang W. Density Functional Theory of Atoms and Molecules. Oxford University Press: New York and Clarendon Press: Oxford, 1989.
50. (a) Nalewajski RF. J. Am. Chem. Soc. 1984; 106: 944-945;
51. (b) De Proft F, Langenaeker W, Geerlings P. J. Mol. Struct. (THEOCHEM) 1995; 339: 45-55.
52. Burkert U, Allinger NL. Molecular Mechanics. American Chemical Society: Washington, DC, 1982.
53. (a) Théry V, Rinaldi D, Rivail J-L, Maigret B, Ferenczy JJ. J. Comput. Chem. 1994; 15: 269-282.
54. Hobza P, Zahradnik R. Intermolecular Complexes. Elsevier: Amsterdam, 1988.
55. (a) Seshu S, Read MB. Linear Graphs and Electrical Networks. Addison-Wesley: Reading, MA. 1961;
56. (b) The Manual on Electrical Engineeing. Energoatomizdat: Moscow, 1985.
57. Golender VE, Drbogiav VV, Rosenblit AB. J. Chem. Inf. Comput. Sci. 1981; 21: 196-204.
58. Oliferenko AA, Palyulin VA, Zefirov NS. Dokl. Chem. 1999; 368: 209-212.
59. Huheey JE. Inorganic Chemistry. Principles of Structure and Reactivity. Harper and Row: New York, 1983.
60. Yang W, Lee G, Ghosh SK. J. Phys. Chem. 1985; 89: 5412-5414.
61. (a) Iczkowski RP, Margrave IL. J. Am. Chem. Soc. 1961; 83: 3547-3551;
62. (b) Jorgenssen CK, Horner SM, Harfield WE, Tyree SY. Int. J. Quantum Chem. 1967; 1: 191-195.
63. Komorowski L. Chem. Phys. 1987; 114: 55-71.
64. (a) Bergman D, Hinze J. Struct. Bonding (Behin) 1987; 66: 145-190;
65. (b) Bergman D, Hinze J. Angew. Chem. Int. Ed. Engl. 1996; 35: 150-163.
66. Slater J. Self-Consistent Field for Molecules and Solids. McGraw-Hill: New York, 1974.
67. Kohn W, Becke AD, Parr RG. J. Chem. Phys. 1996; 100: 12974-12980.
68. Luo Y-R, Benson SW. Acc. Chem. Res. 1992; 25 375-381.
69. Gillespie R, Hargittai I. The VSEPR Model of Molecular Geometry. Allyn and Bacon: Boston, 1991.
70. (a) Wilmshurst JK. J. Chem. Phys. 1959; 30: 561-565;
71. (b) Whitehead MA, Jaffe HH. Theor. Chem. Acta 1963; 1: 209-221.
72. (a) Mulliken RS. J. Chem. Phys. 1952; 51: 295-310;
73. (b) Rue R. Ruedenberg K. J. Phys. Chem. 1964; 68: 1676-1706;
74. (c) Szentpàly LV. J. Phys. Chem. A 1998; 102: 10912-10915.
75. Coulson C. Valence. Oxford University Press: London, 1961.
76. Santry DP, Segal GA. J. Chem. Phys. 1967; 47: 158-174.
77. Oliferenko AA, Pisarev SA, Palyulin VA, Zefirov NS. Bull. Moscow State Univ., Ser. 2, Chem. 2000; 41: 324-326.
78. (a) Randic M, Maksic Z. Theor. Chem. Acta 1965; 3: 59-68;
79. (b) Maksić Z, Klasinc L, Randic M. Theor. Chem. Acta 1966; 4: 273-286.
80. (a) Clementi E, Roetti C. At. Data Nucl. Data Tables 1974; 14: 177-478.
81. Klasinc L, Maksic Z, Randic M. J. Chem. Soc. A 1966; 755-757.
82. Minkin VI, Simkin BYa, Minyaev RN. The Theory of Molecular Structure. Vysshaya Shkola: Moscow, 1979.
83. Gasteiger J, Jochum C. J Chem. Inf. Comput. Sci. 1979; 19: 43-48.
84. Cieplak P, Cornell WD, Bayly C, Kollman PA. J. Comput. Chem. 1995; 16: 1357-1377.
85. Siegbahn K, Nordling C, Johansson G, Hedman J, Heden PF, Hamrin K, Gelius U, Bergmark T, Werne LO, Manne R, Baer Y. ESCA Applied to Free Molecules. North-Holland: Amsterdam, 1969.
86. Jolly WL, Bomben KD, Eyermann CY. At. Data Nucl. Data Tables 1984; 31: 433-493.