The molecular structure of the tris(2-mercapto-l-tolylimidazolyl) hydroborato zinc(2-mercapto-l-tolylimidazole) complex, {[Tmp-Tol] Zn(mimp-Tol)} [ClO4]: Intermolecular N-H⋯OClO 4 versus intramolecular N-H⋯S hydrogen bonding interactions of the mercaptoimidazole ligand

Dalton Transactions

Volumn , Issue 21, 2004, Pages 3448-3452

  Morlok, Melissa M ^a   Docrat, Arefa ^a   Janak, Kevin E ^a   Tanski, Joseph M ^a   Parkin, Gerard ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALKYLATION; CHARGE COUPLED DEVICES; COMPLEXATION; CRYSTALLIZATION; DNA; ENZYMES; HYDROGEN BONDS; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLICS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

DENSITY FUNCTIONAL THEORY (DFT); MERCAPTOIMIDAZOLE LIGANDS; RESONANCE STRUCTURES; THIOKETONES;

ZINC COMPOUNDS;

IMIDAZOLE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; TRIS(2 MERCAPTO 1 TOLYLIMIDAZOLYL)HYDROBORATO ZINC(2 MERCAPTO 1 TOLYLIMIDAZOLE) COMPLEX; TRIS(2-MERCAPTO-1-TOLYLIMIDAZOLYL)HYDROBORATO ZINC(2-MERCAPTO-1-TOLYLIMIDAZOLE) COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; IMIDAZOLES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 9644290763     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412147c     Document Type: Article

References (61)

1. (a) B. L. Vallee and D. S.Auld, Acc. Chem. Res., 1993, 26, 543-551;
2. (b) D. S. Auld, Struct. Bonding (Berlin), 1997, 89, 29-50;
3. (c) J. E. Coleman, Curr. Opin. Chem. Biol., 1998, 2, 222-234;
4. (d) S. Rahuel-Clermont and M. F. Dunn, Copper Zinc Inflamm. Degener. Dis., 1998, 47-59;
5. (e) R. H. Holm, P. Kennepohl and E. I. Solomon, Chem. Rev., 1996, 96, 2239-2314;
6. (f) W. N. Lipscomb and N. Sträter, Chem. Rev., 1996, 96, 2375-2433;
7. (g) S. Lindskog, Phamacoi Ther., 1997, 74, 1-20.
8. (a) W. Maret, Biochemistry, 2004, 43, 3301-3309;
9. (b) S. Iuchi, Cell. Mol. Life Sci. 2001, 58, 625-635;
10. (c) J. M. Berg and Y. Shi, Science, 1996, 271, 1081-1085;
11. (d) J. H. Laity, B. M. Lee and P. E. Wright, Curr. Opin. Struct. Biol, 2001, 11, 39-46;
12. (e) J. M. Berg and H. A. Godwin, Annu. Rev. Biophys. Biomol. Struct., 1997, 26, 357-371.
13. (a) G. Parkin, Chem. Rev., 2004, 104, 699-767;
14. (b) G. Parkin, Chem. Commun., 2000, 1971-1985;
15. G. Parkin, Met. Ions Biol. Syst., 2001, 38, 411-460.
16. (a) L. C. Myers, M. P. Terranova, A. E. Ferentz, G. Wagner and G. L. Verdine, Science, 1993, 261, 1164-1167;
17. (b) L. C. Myers, F. Jackow and G. L. Verdine, J. Biol. Chem., 1995, 270, 6664-6670.
18. A. T. Maynard and D. G. Covell, J. Am. Chem. Soc., 2001, 123, 1047-1058.
19. L. C. Myers, G. L. Verdine and G. Wagner, Biochemistry, 1993, 32, 14089-14094.
20. A. Docrat, M. M. Morlok, B. M. Bridgewater, D. G. Churchill and G. Parkin, Polyhedron, 2004, 23, 481-488.
21. 2R]H.
22. d (a) S.-J. Chiou, C. G. Riordan and A. L. Rheingold, Proc. Natl. Acad. Sci. USA, 2003, 100, 3695-3700; (b) W.-Y. Sun, L. Zhang and K.-B. Yu, J. Chem. Soc. Dalton Trans., 1999, 795-798; (c)X.-F. Shi, W.-Y. Sun, L. Zhang and C.-D. Li, Spectrochim. Acta, Part A, 2000, 56, 603-613; (d) J. N. Smith, Z. Shirin and C. J. Carrano, J. Am. Chem. Soc., 2003,125, 868-869.
23. d (a) S.-J. Chiou, C. G. Riordan and A. L. Rheingold, Proc. Natl. Acad. Sci. USA, 2003, 100, 3695-3700; (b) W.-Y. Sun, L. Zhang and K.-B. Yu, J. Chem. Soc. Dalton Trans., 1999, 795-798; (c)X.-F. Shi, W.-Y. Sun, L. Zhang and C.-D. Li, Spectrochim. Acta, Part A, 2000, 56, 603-613; (d) J. N. Smith, Z. Shirin and C. J. Carrano, J. Am. Chem. Soc., 2003,125, 868-869.
24. d (a) S.-J. Chiou, C. G. Riordan and A. L. Rheingold, Proc. Natl. Acad. Sci. USA, 2003, 100, 3695-3700; (b) W.-Y. Sun, L. Zhang and K.-B. Yu, J. Chem. Soc. Dalton Trans., 1999, 795-798; (c)X.-F. Shi, W.-Y. Sun, L. Zhang and C.-D. Li, Spectrochim. Acta, Part A, 2000, 56, 603-613; (d) J. N. Smith, Z. Shirin and C. J. Carrano, J. Am. Chem. Soc., 2003,125, 868-869.
25. d (a) S.-J. Chiou, C. G. Riordan and A. L. Rheingold, Proc. Natl. Acad. Sci. USA, 2003, 100, 3695-3700; (b) W.-Y. Sun, L. Zhang and K.-B. Yu, J. Chem. Soc. Dalton Trans., 1999, 795-798; (c)X.-F. Shi, W.-Y. Sun, L. Zhang and C.-D. Li, Spectrochim. Acta, Part A, 2000, 56, 603-613; (d) J. N. Smith, Z. Shirin and C. J. Carrano, J. Am. Chem. Soc., 2003,125, 868-869.
26. +, are -2 and -11, respectively. See: (a) G. A. Olah, A. M. White and D. H. O'Brien, Chem. Rev., 1970, 70, 561-591; (b)A. Bagno and G. Scorrano, J. Am. Chem. Soc., 1988, 110, 4577-4582; (c) E. M. Arnett, Prog. Phys. Org. Chem., 1963, 1, 223-403.
27. +, are -2 and -11, respectively. See: (a) G. A. Olah, A. M. White and D. H. O'Brien, Chem. Rev., 1970, 70, 561-591; (b)A. Bagno and G. Scorrano, J. Am. Chem. Soc., 1988, 110, 4577-4582; (c) E. M. Arnett, Prog. Phys. Org. Chem., 1963, 1, 223-403.
28. +, are -2 and -11, respectively. See: (a) G. A. Olah, A. M. White and D. H. O'Brien, Chem. Rev., 1970, 70, 561-591; (b)A. Bagno and G. Scorrano, J. Am. Chem. Soc., 1988, 110, 4577-4582; (c) E. M. Arnett, Prog. Phys. Org. Chem., 1963, 1, 223-403.
29. 2 is -10. See: S. Brownstein and A. E. Stillman, J. Phys. Chem., 1959, 63, 2061-2062.
30. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
31. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
32. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
33. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
34. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
35. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
36. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
37. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
38. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
39. R]ZnX complexes, see: (a) C. Kimblin, B. M. Bridgewater, D. G. Churchill and G. Parkin, Chem. Commun., 1999, 2301-2302; ( b) B. M. Bridgewater and G. Parkin, J. Am. Chem. Soc., 2000, 122, 7140-7141; (c) B. M. Bridgewater and G. Parkin, Inorg. Chem. Commun., 2001, 4, 126-129; (d) B. M. Bridgewater, T. Fillebeen, R. A. Friesner and G. Parkin, J. Chem. Soc., Dalton Trans., 2000, 4494-4496; (e) M. Garner, J. Reglinski, I. Cassidy, M. D. Spicer and A.R.Kennedy, Chem. Commun., 1996, 1975-1976; (f) I. Cassidy, M. Garner, A. R. Kennedy, G. B. S. Potts, J. Reglinski, P. A. Slavin and M. D. Spicer, Eur. J. Inorg. Chem., 2002, 1235-1239; (g) S. Bakbak, V. K. Bhatia, C. D. Incarvito, A. L. Rheingold and D. Rabinovich, Polyhedron, 2001, 20, 3343-3348; (h) J. L. White, J. M. Tanski and D. Rabinovich, J. Chem. Soc., Dalton Trans., 2002, 2987-2991; (i) M. Tesmer, M. Shu and H. Vahrenkamp, Inorg. Chem., 2001, 40, 4022-4029; (J) J. Seebacher and H. Vahrenkamp, J. Mol. Struct., 2003, 656, 177-181.
40. p-Tol ligand with a O⋯O distance of 2.79 Å (see Fig. 2).
41. T. Steiner, Angew. Chem., Int. Ed., 2002, 41, 48-76.
42. The values listed are for interactions in which both O-H⋯N and N - C - Me bond angles are greater than 160°. CSD Version 5.25. 3D Search and Research Using the Cambridge Structural Database, Chemical Design Automation News, ed. F. H. Alien and O. Kennard, 1993, vol. 8(1), pp. 1 & 31-37.
43. S. Brooker, D. J. de Geest, R. J. Kelly, P. G. Plieger, B. Moubaraki, K.S.Murray and G. B. Jameson, J. Chem. Soc., Dalton Trans., 2002, 2080-2087.
44. CCDC deposition code AGACAM.
45. (a)H. T. Flakus, A. Miros and P.G.Jones, Spectrochim. Acta, Part A, 2002, 58, 225-237;
46. (b) G. Vampa, S. Benvenuti, F. Severi, L. Malmusi and L. Antolini, J. Heterocyd Chem., 1995, 32, 227-234.
47. J. L. White, J. M. Tanski, D. G. Churchill, A. L. Rheingold and D. Rabinovich, J. Chem. Crystallogr., 2003, 33, 437-445.
48. F. H. Alien, C. M. Bird, R. S. Rowland and P. R. Raithby, Acta. Crystallogr., Sect. B, 1997, 53, 680-695.
49. 4-o-NHC(O)Me exhibits an intramolecular N-H⋯O hydrogen rather than an N-H⋯S hydrogen bond. See ref. 9d.
50. - indicate that each ring possesses a charge of -0.62. See; J. Reglinski, M. Garner, I. D. ICassidy, P. A. Slavin, M. D. Spicer and D. R. Armstrong, J. Chem. Soc., Dalton Trans., 1999, 2119-2126.
51. G. M. Sheldrick, SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, University of Göttingen, Göttingen, Federal Republic of Germany. 1981.
52. Jaguar 4.1 Schrödinger, Inc., Portland, Oregon, 2001.
53. (a) J. C. Slater, Quantum Theory of Molecules and Solids, Vol. 4; The Self-Consistent Field for Molecules and Solids, McGraw-Hill: New York, 1974;
54. (b) S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200-1211;
55. (c) C. T. Lee, W. T. Yang and R. G. Parr, Phys. Rev. B: Condens. Matter, 1988, 37, 785-789;
56. (d) A. D. Becke, Phys. Rev. A: At. Mol. Opt. Phys., 1988, 38, 3098-3100;
57. (e) A. D. Becke, J. Chem. Phys., 1993, 98, 5648-5652.
58. (a) P. J. Hay and W R. Wadt, J. Chem. Phys., 1985, 82, 299-310;
59. (b) W. R. Wadt and P. J. Hay, J. Chem. Phys., 1985, 82, 284-298;
60. (c) P. J. Hay and W. R Wadt, J. Chem. Phys., 1985, 82, 270-283.
61. T. H. Dunning, J. Chem. Phys., 1989, 90, 1007-1023.