peri-interactions in naphthalenes, 13 [1] 8-Dimethylamino-naphth-1-yl carbinols as model systems for potential N→Si/P interactions

Journal of Molecular Structure

Volumn 751, Issue 1-3, 2005, Pages 172-183

  Dominiak, Paulina M ^a   Petersen, Sönke ^b   Schiemenz, Berthold ^c   Schiemenz, Günter P ^b   Wozniak, Krzysztof ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY OF KIEL   (Germany)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Intramolecular hydrogen bonds; peri Substituted naphthalenes; Steric effects; Weak donor acceptor interactions

Indexed keywords

ALCOHOLS; HYDROGEN BONDS; NITROGEN; PHOSPHORUS; SILICON; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

INTRAMOLECULAR HYDROGEN BONDS; PERI-SUBSTITUTED NAPTHALENES; STERIC EFFECTS; WEAK DONOR/ACCEPTOR INTERACTIONS;

NAPHTHALENE;

EID: 23944476643     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2005.04.042     Document Type: Article

References (88)

1. Part 12: G.P. Schiemenz, Z. Naturforsch. 59b (2004) 807-816.
2. G.P. Schiemenz, R. Bukowski, L. Eckholtz, B. Varnskühler, and Z. Naturforsch 55b 2000 12 20
3. G.P. Schiemenz, and Z. Anorg Allg. Chem. 628 2002 2597 2604
4. Cf., e.g. K. Müller-Dethlefs, and P. Hobza Chem. Rev. 100 2000 143 167
5. G.P. Schiemenz, S. Pörksen, P.M. Dominiak, and K. Woźniak Z. Naturforsch 57b 2002 8 18
6. G.P. Schiemenz, C. Näther, and S. Pörksen Z. Naturforsch 58b 2003 663 671
7. G.P. Schiemenz, B. Schiemenz, S. Petersen, and C. Wolff Chirality 10 1998 180 189
8. G.P. Schiemenz Chem. Listy 92 1998 269 270
9. G.P. Schiemenz Phosphorus, Sulfur Silicon Relat. Elem. 163 2000 185 202
10. G. Dyker, M. Hagel, G. Henkel, M. Köckerling, C. Näther, S. Petersen, and G.P. Schiemenz Z. Naturforsch 56b 2001 1109 1116
11. G.P. Schiemenz, C. Näther, and S. Pörksen Z. Naturforsch 58b 2003 59 73
12. G.P. Schiemenz, S. Pörksen, and C. Näther Z. Naturforsch 55b 2000 841 854
13. G.P. Schiemenz, and C. Näther Z. Naturforsch 57b 2002 309 318
14. G.P. Schiemenz, S. Petersen, S. Pörksen, Z. Naturforsch. 58b (2003) 715-724. Erratum: On p. 721, right column, line 3, replace [2] by [5].
15. P. Kilian, H.L. Milton, A.M.Z. Slawin, and J.D. Woollins Inorg. Chem. 43 2004 2252 2260
16. S.S. Batsanov Izvest. Akad. Nauk, Ser. Khim. 1995 24 29
17. S.S. Batsanov Russian Chem. Bull. 44 1995 18 23
18. C. Brelière, F. Carré, R.J.P. Corriu, M. Poirier, G. Royo, and J. Zwecker Organometallics 8 1989 1831 1833
19. F. Carré, G. Cerveau, C. Chuit, R.J.P. Corriu, N.K. Nayyar, and C. Réyé Organometallics 9 1989 1989 1991
20. F. Carré, G. Cerveau, C. Chuit, R.J.P. Corriu, and C. Réyé Angew. Chem. 101 1989 474 476
21. F. Carré, G. Cerveau, C. Chuit, R.J.P. Corriu, and C. Réyé Angew. Chem. Int. Ed. Engl. 28 1989 489
22. F. Carré, G. Cerveau, C. Chuit, R.J.P. Corriu, and C. Réyé N. J. Chem. (Nouv. J. Chim.) 16 1992 63 69
23. K. Boyer-Elma, F.H. Carré, R.J.-P. Corriu, and W.E. Douglas J. Chem. Soc., Chem. Commun. 1995 725 726
24. K. Tamao, K. Nagata, M. Asahara, A. Kawachi, Y. Ito, and M. Shiro J. Am. Chem. 117 1995 11592 11593
25. K. Tamao, M. Asahara, and A. Kawachi J. Organomet. Chem 521 1996 325 334
26. K. Tamao, M. Asahara, Guang-Ri Sun, and A. Kawachi J. Organomet. Chem. 574 1999 193 205
27. K. Tamao, M. Asahara, and A. Toshimitsu Chem. Lett. 2000 658 659
28. K. Tamao, M. Asahara, T. Saeki, Shengyu Feng, A. Kawachi, and A. Toshimitsu Chem. Lett. 2000 660 661
29. M. Spiniello, and J.M. White Organometallics 19 2000 1350 1354
30. K. Tamao, M. Asahara, A. Kawachi, and A. Toshimitsu J. Organomet. Chem. 643-644 2002 479 486
31. 300 pm
32. K. Tamao, M. Asahara, T. Saeki, and A. Toshimitsu Chem. Lett. 1999 335 336
33. M.J. Hanson, M. Spiniello, and J.M. White J. Organomet. Chem. 654 2002 3 7
34. C. Brelière, F. Carré, R.J.P. Corriu, G. Royo, M. Wong Chi Man, and J. Lapasset Organometallics 13 1994 307 314
35. K. Tamao, M. Asahara, T. Saeki, and A. Toshimitsu Angew. Chem. 111 1999 3520 3523
36. K. Tamao, M. Asahara, T. Saeki, and A. Toshimitsu Angew. Chem. Int. Ed. 38 1999 3316 3318
37. H.W.W. Ehrlich Acta Crystallogr. 10 1957 699 705
38. C. Chuit, R.J.P. Corriu, P. Monforte, C. Reyé, J.-P. Declercq, and A. Dubourg Angew. Chem. 105 1993 1529 1531
39. C. Chuit, R.J.P. Corriu, P. Monforte, C. Reyé, J.-P. Declercq, and A. Dubourg Angew. Chem. Int. Ed. Engl. 32 1993 1430
40. F. Carré, C. Chuit, R.J.P. Corriu, A. Mehdi, and C. Reyé Inorg. Chim. Acta 250 1996 21 28
41. C. Chuit, R.J.P. Corriu, and C. Reyé K.-y. Akiba Chemistry of Hypervalent Compounds 1999 Wiley New York 81 146
42. M. Chauhan, C. Chuit, R.J.P. Corriu, C. Reyé, J.-P. Declercq, and A. Dubourg J. Organomet. Chem. 510 1996 173 179
43. C. Chuit, and C. Reyé Eur. J. Inorg. Chem. 1998 1847 1857
44. R.O. Day, T.K. Prakasha, R.R. Holmes, and H. Eckert Organometallics 13 1994 1285 1293 (p. 1290)
45. T.K. Prakasha, S. Srinivasan, A. Chandrasekaran, R.O. Day, and R.R. Holmes J. Am. Chem. Soc. 117 1995 10003 10009 (p. 10006)
46. N.V. Timosheva, A. Chandrasekaran, R.O. Day, and R.R. Holmes Inorg. Chem. 37 1998 4945 4952
47. R.W. Alder, A.G. Orpen, and R.B. Sessions J. Chem. Soc. Chem. Commun. 1983 999 1000
48. H. Bock, T. Vaupel, C. Näther, K. Ruppert, and Z. Havlas Angew. Chem. 104 1992 348 350
49. H. Bock, T. Vaupel, C. Näther, K. Ruppert, and Z. Havlas Angew. Chem. Int. Ed. Engl. 31 1992 299 301
50. H. Bock, T. Vaupel, and H. Schödel J. Prakt. Chem. 339 1997 26 37
51. Z. Malarski, T. Lis, E. Grech, J. Nowicka-Scheibe, and K. Majewska J. Mol. Struct. 221 1990 227 238
52. K. Wozniak, T.M. Krygowski, B. Kariuki, W. Jones, and E. Grech J. Mol. Struct. 240 1990 111 118
53. H.A. Staab, C. Krieger, G. Hieber, and K. Oberdorf Angew. Chem. 109 1997 1946 1949
54. H.A. Staab, C. Krieger, K. Hieber, and K. Oberdorf Angew. Chem. Int. Ed. Engl. 36 1997 1884 1886
55. + hydrogen bond reported so far, d(N⋯N) =246.4 pm, has exactly the same length as PD: R. Destro, T. Pilati, M. Simonetta, and E. Vogel J. Am. Chem. Soc. 107 1985 3185 3191
56. T. Steiner Chem. Commun. 1999 313 314
57. W. Klyne, and V. Prelog Experientia 16 1960 521 523
58. J. Rigaudy, and S.P. Klesney International Union of Pure and Applied Chemistry, Organic Chemistry Division, Commission on Nomenclature of Organic Chemistry: Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F and H 1982 Pergamon Press Oxford 484 Cf.
59. S. Kane, and W.H. Hersh J. Chem. Educ. 77 2000 1366
60. E. Grech, J. Nowicka-Scheibe, Z. Olejnik, T. Lis, Z. Pawelka, Z. Malarski, and L. Sobczyk J. Chem. Soc., Perkin Trans. II 1996 343 348
61. A. Toshimitsu, T. Saeki, and K. Tamao Chem. Lett. 2002 278 279
62. T. Herbst, G.P. Schiemenz, and C. Wolff Magn. Reson. Chem. 26 1988 608 611
63. T. Herbst, and G.P. Schiemenz Z. Naturforsch 44b 1989 866 868
64. W.B. Schweizer, G. Procter, M. Kaftory, and J.D. Dunitz Helv. Chim. Acta 61 1978 2783 2808
65. J. Clayden, C. McCarthy, and M. Helliwell Chem. Commun. 1999 2059 2060
66. Cf. D. Casarini, L. Lunazzi, and A. Mazzanti J. Org. Chem. 62 1997 3315 3323
67. T. Steiner, C.C. Wilson, and I. Majerz Chem. Commun. 2000 1231 1232
68. Cf. T Steiner Chem. Commun. 1999 2299 2300
69. V.R. Pedireddi, and G.R. Desiraju J. Chem. Soc., Chem. Commun. 1992 988 990
70. G.R. Desiraju Angew. Chem. 107 1995 2541 2558
71. G.R. Desiraju Angew. Chem. Int. Ed. Engl. 34 1995 2311 2327
72. V.R. Thalladi, A. Gehrke, and R. Boese New J. Chem. 2000 463 470
73. C. Chuit, R.J.P. Corriu, P. Monforte, C. Reyé, J.-P. Declercq, and A. Dubourg J. Organomet. Chem. 511 1996 171 175
74. T. Barth, C. Krieger, F.A. Neugebauer, and H.A. Staab Angew. Chem. 103 1991 1006 1008
75. T. Barth, C. Krieger, F.A. Neugebauer, and H.A. Staab Angew. Chem. Int. Ed. Engl. 30 1991 1028
76. K. Wozniak, H. He, J. Klinowski, B. Nogaj, D. Lemanski, D.E. Hibbs, M.B. Hursthouse, and S.T. Howard J. Chem. Soc., Faraday Trans. 91 1995 3925 3932
77. A. Karaçar, H. Thönnessen, P.G. Jones, R. Bartsch, and R. Schmutzler Heteroatom Chem. 8 1997 539 550
78. D. Casarini, L. Lunazzi, A. Mazzanti, and E. Foresti J. Org. Chem. 63 1998 4746 4754
79. A. Karaçar, M. Freytag, H. Thönnessen, J. Omelanczuk, P.G. Jones, R. Bartsch, R. Schmutzler, and Z. Anorg Allg. Chem. 626 2000 2361 2372
80. Schmutzler et al. used older r(vdW) data and thus arrived at much more impressive differences. Besides other arguments, the poor precision of r(vdW) values invalidates Holmes's procedure of calculating degrees of hypercoordination [21].
81. S. Petersen, Diploma thesis, University of Kiel, 1993.
82. M. Hesse, H. Meier, and B. Zeeh Spektroskopische Methoden in der organischen Chemie 4th ed. 1991 Thieme Stuttgart p. 96
83. C. Brelière, R.J.P. Corriu, G. Rojo, and J. Zwecker Organometallics 8 1989 1834 1836
84. S. Petersen, PhD thesis, University of Kiel 1999.
85. 2, R= Et, iPr, in solution do not form such bonds (δ(H-O) 1.97, 1.82) [33].
86. G.M. Sheldrick Acta Crystallogr. A 46 1990 467 473
87. G.M. Sheldrick, SHELXL97. Program for the Refinement of Crystal Structures, University of Göttingen, Germany.
88. A.J.C. Wilson International Tables for Crystallography vol. C 1992 Kluwer Dordrecht