Empirical LCAO parameters π for molecular orbitals in planar organic molecules

Molecular Physics

Volumn 107, Issue 17, 2009, Pages 1755-1771

  Hawke, L G D ^a   Kalosakas, G ^a   Simserides, C ^b  

^a UNIVERSITY OF PATRAS   (Greece)

^b INSTITUTE OF MATERIALS SCIENCE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL CALCULATION; AZABENZENES; DIAGONAL MATRIX ELEMENTS; EMPIRICAL PARAMETERS; NUCLEIC ACID BASIS; ORBITALS; ORGANIC MOLECULES; OXYGEN ATOM; PARAMETRIZATIONS; POLYACENES; TRANSITION ENERGY;

ALDEHYDES; ATOMS; BENZENE; BOND LENGTH; KETONES; MOLECULAR MODELING; MOLECULAR ORBITALS; MOLECULAR OXYGEN; MOLECULES; NITROGEN; NUCLEIC ACIDS;

AROMATIC HYDROCARBONS;

EID: 68949113710     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268970903049089     Document Type: Article

References (183)

1. B. Alberts, D. Bray, K. Hopkin, and A. Johnson, Essential Cell Biology, 2nd ed. (Garland Science Publishing, New York, NY, 2004).
2. (a) R.A. Morton and G.A.J. Pitt, Adv. Enzymol. Relat. Sub. & Biochem. 32, 97 (1969);
3. (b) E.W. Abrahamson and S.E. Ostroy, Progr. Biophys. Mol. Biol. 17, 179 (1967).
4. G. Horowitz, Adv. Matter 10, 365, and references therein (1998).
5. F.F. Heyroth and J.R. Loofbourow, J. Am. Chem. Soc. 56, 1728 (1934).
6. E.P. Carr and H. Stü cklen, J. Chem. Phys. 4, 760 (1936).
7. V. Henri and L.W. Pickett, J. Chem. Phys. 7, 439 (1939).
8. J.R. Platt and H.B. Klevens, J.Chem. Phys. 16, 832 (1948).
9. J.R. Platt, H.B. Klevens, and W.C. Price, J. Chem. Phys. 17, 466 (1949).
10. H.B. Klevens and J.R. Platt, J. Chem. Phys. 17, 470 (1949).
11. R.A. Friedel, M. Orchin, and L. Reggel, J. Am. Chem. Soc. 70, 199 (1948).
12. L. Doub and J.M. Vandenbelt, J. Am. Chem. Soc. 71, 2414 (1949).
13. L. Doub and J.M. Vandenbelt, J. Am. Chem. Soc. 69, 2714 (1947).
14. (a) F. Halverson and R.C. Hirt, J. Chem. Phys. 19, 711 (1951);
15. (b) R.C. Hirt, F. Halverson, and R.G. Schmitt, J. Chem. Phys. 22, 1148 (1954).
16. (a) J.T. Gary and L.W. Pickett, J. Chem. Phys. 22, 599 (1954);
17. (b) L.C. Jones and L.W. Taylor, Anal. Chem. 27, 228 (1955);
18. (c) G.R. Hunt and I.G. Ross, J. Mol. Spectrosc. 9, 50 (1962).
19. P.A. Mullen and M.K. Orloff, J. Chem. Phys. 51, 2277 (1969).
20. W.M. Flicker, O.A. Mosher, and A. Kuppermann, Chem. Phys. Lett. 45, 492 (1977).
21. C.D. Cooper, A.D. Williamson, J.C. Miller, and R.N. Compton, J. Chem. Phys. 73, 1527 (1980).
22. I.C. Walker, T.M. Abuain, M.H. Palmer, and A.J. Beveridge, Chem. Phys. 109, 269 (1986).
23. M.H. Palmer, A.J. Beveridge, I.C. Walker, and T.M. Abuain, Chem. Phys. 117, 51 (1987).
24. A.G. Robinson, P.R. Winter, and T.S. Zwier, J. Chem. Phys. 116, 7918 (2002).
25. E. Hü ckel, Z. Phys. 70, 204, Z. Phys. 76, 628 (1932) (1931).
26. W. Kutzelnigg, J. Comput. Chem. 28, 25 (2007).
27. J.R. Platt, J. Chem. Phys. 18, 1168 (1950).
28. J.R. Platt, J. Chem. Phys. 19, 101 (1951).
29. R. Pariser and R.G. Parr, J. Chem. Phys. 21, 466 (1953).
30. R. Pariser and R.G. Parr, J. Chem. Phys. 21, 767 (1953).
31. R. Pariser, J. Chem. Phys. 24, 250 (1956).
32. N.O. Lipari and C.B. Duke, J. Chem. Phys. 63, 1768 (1975).
33. J.E. Del Bene, J.D. Watts, and R.J. Bartlett, J. Chem. Phys. 106, 6051 (1997).
34. H.H. Heinze, A. Gö rling, and N. Rö sch, J. Chem. Phys. 113, 2088 (2000).
35. E.S. Kadantsev, M.J. Stott, and A. Rubio, J. Chem. Phys. 124, 134901 (2006).
36. R.G. Endres, C.Y. Fong, L.H. Yang, G. Witte, and Ch. Wö ll, Computat. Mater. Sci. 29, 362 (2004).
37. (a) A.B. Trofimov and J. Schirmer, Chem. Phys. 214, 153 (1997);
38. (b) O. Christiansen, J. Gauss, J.F. Stanton, and P. Jørgensen, J. Chem. Phys. 111, 525 (1999).
39. J. Wan, J. Meller, M. Hada, M. Ehara, and H. Nakatsuji, J. Chem. Phys. 113, 7853 (2000).
40. M. Boggio-Pasqua, M.J. Bearpark, M. Klene, and M.A. Robb, J. Chem. Phys. 120, 7849 (2004).
41. L. Serrano-Andres, R. Pou-Amé rigo, M.P. Fü lscher, and A.C. Borin, J. Chem. Phys. 117, 1649 (2002).
42. (a) W.A. Harrison, Electronic Structure and the Properties of Solids, 2nd ed. (Dover, New York, 1989);
43. (b) W.A. Harrison, Elementary Electronic Structure(World Scientific, River Edge, NJ, 1999).
44. A. Streitwieser, Molecular Orbital Theory for Organic Chemists (Wiley, New York, 1961).
45. (a) T. Cramer, S. Krapf, and T. Koslowski, J. Phys. Chem. B 108, 11812 (2004);
46. (b) T. Cramer, S. Krapf, and T. Koslowski, J. Phys. Chem. C 111, 8105 (2007).
47. M. Wolfsberg and L. Helmholz, J. Chem. Phys. 20, 837 (1952).
48. NIST Chemistry Webbook (http://webbook.nist.gov/ chemistry/) and references therein. The coordinates of the nucleic acids bases are obtained from http:// chemistry.gsu.edu/Glactone/PDB/pdb.html
49. B.O. Roos, M.P. Fulscher, P.-A. Malmqvist, M. Merchan, and L. Serrano-Andres, in Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy, edited by S.R. Langhoff (Kluwer Academic, Amsterdam, 1995).
50. S. Grimme and M. Parac, Tech. Rep. Ser.- I. A. E. A. 4, 292 (2003).
51. J.O. Howell, J.M. Goncalves, C. Amatore, L. Klasinc, R.M. Wightman, and J.K. Kochi, J. Am. Chem. Soc. 106, 3968 (1984).
52. B. Kovac, M. Mohraz, E. Heilbronner, V. Boekelheide, and H. Hopf, J. Am. Chem. Soc. 102, 4314 (1980).
53. W. Kaim, H. Tesmann, and H. Bock, Chem. Ber. 113, 3221 (1980).
54. T. Kobayashi, Phys. Lett. 69, 105 (1978).
55. L. Klasinc, I. Novak, M. Scholz, and G. Kluge, Croat. Chem. Acta. 51, 43 (1978).
56. W. Schmidt, J. Chem. Phys. 66, 828 (1977).
57. E. Clar and W. Schmidt, Tetrahedron. 32, 2563 (1976).
58. P.K. Bischof, M.J.S. Dewar, D.W. Goodman, and T.B. Jones, J. Organomet. Chem. 82, 89 (1974).
59. M. Klessinger, Angew. Chem. Int. Ed. Engl. 11, 525 (1972).
60. H. Bock, G. Wagner, and J. Kroner, Chem. Ber. 105, 3850 (1972).
61. R. Gleiter, E. Heilbronner, and V. Hornung, Angew. Chem. Int. Edn 9, 901 (1970).
62. (a) J.A. Sell and A. Kupperman, Chem. Phys. 33, 367 (1978);
63. (b) M. Gower, L.A.P. Kane-Maguire, J.P. Maier, and D.A. Sweigart, J. Chem. Soc. Dalton Trans. 316 (1977);
64. (c) H. Bock, W. Kaim, and H.E. Rohwer, J. Organomet. Chem. 135, 14 (1977);
65. (d) T. Kobayashi and S. Nagakura, J. Electron Spectrosc. Relat. Phenom. 7, 187 (1975);
66. (e) W. Schafer and A. Schweig, Angew. Chem. 84, 898 (1972);
67. (f) T.A. Carlson and C.P. Anderson, Chem. Phys. Lett. 10, 561 (1971);
68. (g) H. Bock and W. Fuss, Angew. Chem. Int. Edn Engl. 10, 182 (1971).
69. C.N.R. Rao, Ultra-violet and Visible Spectroscopy: Chemical Applications (Butterworth, London, 1975).
70. H.H. Perkampus, UV-VIS Atlas of Organic Compounds(VCH, Weinheim, 1992).
71. L. Klasinc, B. Kovac, and H. Gusten, Pure Appl. Chem. 55, 289 (1983).
72. E. Heilbronner, T. Hoshi, J.L. von Rosenberg, and K.T. Hafner, Nouv. J. Chim. 1, 105 (1976).
73. F. Marschner and H. Goetz, Tetrahedron. 30, 3159 (1974).
74. H. Bock and G. Wagner, Angew. Chem. Int. Edn Engl. 11, 119 (1972).
75. N.S. Hush, A.S. Cheung, and P.R. Hilton, J. Electron Spectrosc. Relat. Phenom. 7, 385 (1975).
76. (a) L. Klasinc, B. Kovac, S. Schoof, and H. Gusten, Croat. Chem. Acta. 51, 307 (1978);
77. (b) C. Jongsma, H. Vermeer, F. Bickelhaupt, W. Schä fer, and A. Schweig, Tetrahedron. 31, 2931 (1975);
78. (c) W. Schafer, A. Schweig, F. Bickelhaupt, and H. Vermeer, Angew. Chem. Int. Edn Engl. 11, 924 (1972).
79. I. Akiyama, K.C. Li, P.R. LeBreton, P.P. Fu, and R.G. Harvey, J. Phys. Chem. 83, 2997 (1979).
80. B. Ruscic, B. Kovac, L. Klasinc, and H. Gusten, Z. Naturforsch. A 33, 1006 (1978).
81. J.P. Maier and D.W. Turner, Faraday Discuss. Chem. Soc. 54, 149 (1972).
82. F. Brogli and E. Heilbronner, Angew. Chem. Int. Ed. Engl. 11, 538 (1972).
83. D. Biermann and W. Schmidt, J. Am. Chem. Soc. 102, 3173 (1980).
84. N. Nijegorodov, V. Ramachandran, and D.P. Winkoun, Spectrochim. Acta Part A. 53, 1813 (1997).
85. (a) E. Clar and W. Schmidt, Tetrahedron. 33, 2093 (1977);
86. (b) R. Boschi and W. Schmidt, Tetrahedron Lett. 25, 2577 (1972).
87. C. Pentrongolo, R.J. Buenker, and S.D. Peyerimhoff, J. Chem. Phys. 76, 3655 (1982).
88. L.E. McMurchie and E.R. Davidson, J. Chem. Phys. 67, 5613 (1977).
89. R. Lindh and B.O. Roos, Int. J. Quantum Chem. 35, 813 (1989).
90. L. Serrano-Andres, M. Merchá n, I. Nebot-Gil, R. Lindh, and B.O. Roos, J. Chem. Phys. 98, 3151 (1993).
91. A. Kuppermann, W.M. Flicker, and O.A. Mosher, Chem. Reviews 79, 77 (1979).
92. D.A. Krause, J.W. Taylor, and R.F. Fenske, J. Am. Chem. Soc. 100, 718 (1978).
93. R.M. White, T.A. Carlson, and D.P. Spears, J. Electron Spectrosc. Relat. Phenom. 3, 59 (1974).
94. G. Bieri and L. Asbrink, J. Electron Spectrosc. Relat. Phenom. 20, 149 (1980).
95. J. Merer and R.S. Mulliken, Chem. Rev. 69, 639 (1969).
96. K. Kimura, S. Katsumata, T. Yamazaki, and H. Wakabayashi, J. Electron Spectrosc. Relat. Phenom. 6, 41 (1975).
97. (a) G. Hentrich, E. Gunkel, and M. Klessinger, J. Mol. Struct. 21, 231 (1974);
98. (b) U. Weidner and A. Schweig, J. Organomet. Chem. 39, 261 (1972).
99. P. Mollere, H. Bock, G. Becker, and G. Fritz, J. Organomet. Chem. 46, 89 (1972).
100. K.B. Wiberg, G.B. Ellison, J.J. Wendoloski, C.R. Brundle, and N.A. Kuebler, J. Am. Chem. Soc. 98, 7179 (1976).
101. T. Koenig, T. Balle, and W. Snell, J. Am. Chem. Soc. 97, 662 (1975).
102. (a) E.J. McAlduff and K.N. Houk, Can. J. Chem. 55, 318 (1977);
103. (b) P.D. Mollere, K.N. Houk, D.S. Bomse, and T.H. Morton, J. Am. Chem. Soc. 98, 4732 (1976); (c) W. Fuss and H. Bock, J. Chem. Phys. 61, 1613 (1974).
104. H. Schmidt and A. Schweig, Tetrahedron. 32, 2239 (1976).
105. O.A. Mosher, W.M. Flicker, and A. Kuppermann, Chem. Phys. Lett. 19, 332 (1973); J. Chem. Phys. 59, 6502 (1973).
106. R. McDiarmid, Chem. Phys. Lett. 34, 130 (1975).
107. R.M. Gavin and S.A. Rice, J. Chem. Phys. 60, 3231 (1974).
108. (a) F. Marschner and H. Goetz, Tetrahedron. 30, 3451 (1974);
109. (b) T. Kobayashi and S. Nagakura, Chem. Lett. 903 (1972).
110. J.B. Lambert,H.F. Shurvell, andD.A. Liqhtner,Organic Stuctural Spectroscopy (Prentice-Hall, Upper Saddle River, 1998).
111. (a) P. Bruckmann and M. Klessinger, Chem. Ber. 107, 1108 (1974);
112. (b) T. Kobayashi, K. Yokota, and S. Nagakura, J. Electron Spectrosc. Relat. Phenom. 3, 449 (1973);
113. (c) E.W. Fu and R.C. Dunbar, J. Am. Chem. Soc. 100, 2283 (1978).
114. J. Wan and H. Nakatsuji, Chem. Phys. 302, 125 (2004).
115. T. Koenig, M. Tuttle, and R.A. Wielesek, Tetrahedron Lett. 15, 2537 (1974).
116. F. Brogli, E. Giovannini, E. Heilbronner, and R. Schurter, Chem. Ber. 106, 961 (1973).
117. R. Gleiter, H. Hopf, M. Eckert-Maksic, and K.L. Noble, Chem. Ber. 113, 3401 (1980).
118. T. Koenig, R. Wielesek, W. Snell, and W. Balle, J. Am. Chem. Soc. 97, 3225 (1975).
119. J.P. Maier and D.W. Turner, J. Chem. Soc. Faraday Trans. 2 (69), 196 (1973).
120. (a) R. Gleiter, W. Schafer, and M. Eckert-Maksic, Chem. Ber. 114, 2309 (1981);
121. (b) Y.V. Chizhov, M.M. Timoshenko, V.I. Kleimenov, Y.A. Borisov, G.P. Zolnikova, D.N. Kravtsov, and I.I. Kritskaya, J. Struct. Chem. 27, 401 (1986).
122. D. Dougherty, J. Lewis, R.V. Nauman, and S.P. McGlynn, J. Electron Spectrosc. Relat. Phenom. 19, 21 (1980).
123. Y. Lou, J. Chang, J. Jorgensen, and D.M. Lemal, J. Am. Chem. Soc. 124, 15302 (2002).
124. T. Kobayashi, Bull. Chem. Soc. Jpn 56, 3224 (1983).
125. M. Shahbaz, S. Urano, P.R. LeBreton, M.A. Rossman, R.S. Hosmane, and N.J. Leonard, J. Am. Chem. Soc. 106, 2805 (1984).
126. A. Bolovinos, P. Tsekeris, J. Philis, E. Pantos, and G. Andritsopoulos, J. Mol. Spectrosc. 103, 240 (1984).
127. K.K. Innes, I.G. Ross, and W.R. Moomaw, J. Mol. Spectroscopy 132, 492 (1988).
128. (a) C. Batich, E. Heilbronner, V. Hornung, A.J. Ashe, D.T. Clark, U.T. Cobley, D. Kilcast, and I. Scanlan, 1770 L.G.D. Hawke et al. J. Am. Chem. Soc. 95, 928 (1973);
129. (b) E. Heilbronner, V. Hornung, F.H. Pinkerton, and S.F. Thames, Helv. Chim. Acta. 55, 289 (1972).
130. S. Cradock, R.H. Findlay, and M.H. Palmer, Tetrahedron. 29, 2173 (1973).
131. B.G. Ramsey, J. Org. Chem. 44, 2093 (1979).
132. V.Y. Young and L. Cheng, J. Chem. Phys. 65, 3187 (1976).
133. K. Johnson, I. Powis, and C.J. Danby, Chem. Phys. 70, 329 (1982).
134. P.R. Olivato, S.A. Guerrero, A. Modelli, G. Granozzi, D. Jones, and G. Distefano, J. Chem. Soc. Perkin Trans. II. 1505 (1984).
135. D. Dougherty and S.P. McGlynn, J. Am. Chem. Soc. 99, 3234 (1977).
136. R.P. Amerigo, M. Merchá n, and E. Orti, J. Chem. Phys. 110, 9536 (1999).
137. M. Merchá n, B.O. Roos, R. McDiarmid, and X. Xing, J. Chem. Phys. 104, 1791 (1996).
138. C.R. Silva and J.P. Reilly, J. Phys. Chem. 100, 17111 (1996).
139. T. Koenig, M. Smith, and W. Snell, J. Am. Chem. Soc. 99, 6663 (1977).
140. E.W. Garbisch Jr and R.F. Sprecher, J. Am. Chem. Soc. 88, 3433 (1966).
141. V. Eck, A. Schweig, and H. Vermeer, Tetrahedron Lett. 27, 2433 (1978).
142. A.D. Baker, D.P. May, and D.W. Turner, J. Chem. Soc. B, 22 (1968).
143. C.M. Hadal, J.B. Foresman, and K.B. Wiberg, J. Phys. Chem. 97, 4293 (1993).
144. H.P. Trommsdorff, J. Chem. Phys. 56, 5358 (1972).
145. M.P. Fü lscher, L. Serrano-André s, and B.O. Roos, J. Am. Chem. Soc. 119, 6168 (1997).
146. B. Mennucci, A. Toniolo, and J. Tomasi, J. Phys. Chem. A. 105, 4749 (2001).
147. A.L. Sobolewski and W. Domcke, Eur. Phys. J. D 20, 369 (2002).
148. C.E. Crespo-Herná ndez, C. Marai and B. Kohler, unpublished results.
149. N. Ismail, L. Blancafort, M. Olivucci, B. Kohler, and M.A. Robb, J. Am. Chem. Soc. 124, 6818 (2002).
150. M.K. Shukla and J. Leszczynski, J. Phys. Chem. A. 106, 11338 (2002).
151. M.P. Fü lscher and B.O. Roos, J. Am. Chem. Soc. 117, 2089 (1995).
152. J. Lorentzon, M.P. Fü lscher, and B.O. Roos, J. Am. Chem. Soc. 117, 9265 (1995).
153. M.K. Shukla and P.C. Mishra, Chem. Phys. 240, 319 (1999).
154. A. Broo, G. Pearl, and M.C. Zerner, J. Phys. Chem. A 101, 2478 (1997).
155. C.M. Marian, F. Schneider, M. Kleinschmidt, and J. Tatchen, Eur. Phys. J. D 20, 357 (2002).
156. N.S. Hush and A.S. Cheung, Chem. Phys. Lett. 34, 11 (1975).
157. (a) J. Lin, C. Yu, S. Peng, I. Akiyama, K. Li, L.K. Lee, and P.R. LeBreton, J. Am. Chem. Soc. 102, 4627 (1980);
158. (b) J. Lin, C. Yu, S. Peng, I. Akiyama, K. Li, L.K. Lee, and P.R. LeBreton, J. Phys. Chem. 84, 1006 (1980);
159. (c) S. Peng, A. Padva, and P.R. LeBreton, Proc. Nat. Acad. Sci. USA 73, 2966 (1976).
160. D. Voet, W.B. Gratzer, R.A. Cox, and P. Doty, Biopolymers 1, 193 (1963).
161. T. Yamada and H. Fukutome, Biopolymers 6, 43 (1968).
162. Y. Matsuoka and B. Norden, J. Phys. Chem. 86, 1378 (1982).
163. L.B. Clark, J. Phys. Chem. 94, 2873 (1990).
164. W. Voelter, R. Records, E. Bunnenberg, and C. Djerassi, J. Am. Chem. Soc. 90, 6163 (1968).
165. C.A. Sprecher and W.C. Johnson, Biopolymers 16, 2243 (1977).
166. W.C. Brunner and M.F. Maestre, Biopolymers 14, 555 (1975).
167. L.B. Clark, J. Am. Chem. Soc. 99, 3934 (1977).
168. D. Dougherty, K. Wittel, J. Meeks, and S.P. McGlynn, J. Am. Chem. Soc. 98, 3815 (1976).
169. G. Lauer, W. Schafer, and A. Schweig, Tetrahedron Lett. 45, 3939 (1975).
170. D.W. Miles, M.J. Robins, R.K. Robins, M.W. Winkley, and L. Kittler, J. Am. Chem. Soc. 91, 824 (1969).
171. K. Raksanyi, I. Foldvary, J. Fidy, and L. Kittler, Biopolymers 17, 887 (1978).
172. F. Zaloudek, J.S. Novros, and L.B. Clark, J. Am. Chem. Soc. 107, 7344 (1985).
173. A.F. Fucaloro and L.S. Forster, J. Am. Chem. Soc. 93, 6443 (1971).
174. (a) M.H. Palmer, I. Simpson, and R.J. Platenkamp, J. Mol. Struct. 66, 243 (1980);
175. (b) A. Padva, P.R. LeBreton, R.J. Dinerstein, and J.N.A. Ridyard, Biochem. Biophys. Res. Commun. 60, 1262 (1974).
176. (a) M. Menon and R.E. Allen, Phys. Rev. B 38, 6196 (1988);
177. (b) N. Lathiotakis and A.N. Andriotis, Solid State Commun. 87, 871 (1993);
178. (c) M. Menon, J. Connolly, N. Lathiotakis, and A. Andriotis, Phys. Rev. B 50, 8903 (1994).
179. J.C. Slater and G.F. Koster, Phys. Rev. 94, 1498 (1954).
180. R.G. Endres, D.L. Cox, and R.R.P. Singh, Rev. Mod. Phys. 76, 195 (2004).
181. L.G.D. Hawke, G. Kalosakas and C. Simserides, preprint.
182. L.G.D. Hawke, C. Simserides and G. Kalosakas, Mater. Sci. Eng. B, in press (2009). doi:10.1016/ j.mseb.2009.02.012.
183. T.R. Prytkova, D.N. Beratan, and S.S. Skourtis, Proc. Natl. Acad. Sci. 104, 802 (2007).