Theoretical and spectroscopic studies on molecular structure and hydrogen bonding of 1,2-bis (monochloroacetyl) cyclopentadiene

Journal of Molecular Structure

Volumn 1038, Issue , 2013, Pages 177-187

  Tayyari, Sayyed Faramarz ^a   Laleh, Somayeh ^b   Zahedi Tabrizi, Mansoureh ^c   Vakili, Mohammad ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

^c ALZAHRA UNIVERSITY   (Iran)

Author keywords

1,2 Bis (monochloroacetyl) cyclopentadiene; Density functional theory; Intramolecular hydrogen bond; Rotation barriers; Strong hydrogen bond; Vibrational spectra

Indexed keywords

CHELATION; CHEMICAL SHIFT; DENSITY FUNCTIONAL THEORY; MOLECULAR STRUCTURE; OLEFINS; QUANTUM CHEMISTRY; SPECTROSCOPIC ANALYSIS; VIBRATIONAL SPECTRA;

CYCLOPENTADIENES; DENSITY FUNCTIONAL THEORY CALCULATIONS; HARMONIC VIBRATIONAL WAVENUMBERS; INTRA-MOLECULAR HYDROGEN BONDS; INTRAMOLECULAR HYDROGEN BONDING; NUCLEAR MAGNETIC RESONANCE CHEMICAL SHIFTS; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS; ROTATION BARRIERS;

HYDROGEN BONDS;

EID: 84961985283     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2013.01.031     Document Type: Article

References (53)

1. C.C. Chen, and S.F. Shyu Int. J. Quantum Chem. 76 2000 541 551
2. R.S. Haddon J. Am. Chem. Soc. 102 1980 1807 1811
3. J. Higgins, Z. Zhou, L. Liu, and T.T.S. Huang J. Phys. Chem. A 101 1997 2702 2708
4. N.I. Giricheva, G.V. Girichev, S.B. Lapshina, and N.I. Kuzmina J. Struct. Chem. 41 2000 48 54
5. V.B. Delchev, H. Mikosch, and G.S. Nikolov Monatshefte fur Chemie 132 2001 339 348
6. M. Huang, J. Zou, D. Yang, B. Ning, Zh. Shang, and Q. Yu J. Mol. Struct. (Theochem) 589 2002 321 328
7. V.B. Delchev, and G.S. Nikolov Monatshefte fur Chemie 131 2000 99 105
8. S.F. Tayyari, A. Najafi, F. Lorestani, and R.E. Sammelson J. Mol. Struct. (Theochem) 854 2008 54 62
9. G. Gilli, F. Bellucci, V. Ferretti, and V. Bertolasi J. Am. Chem. Soc. 111 1989 1023 1028
10. J.A. Gerlt, and P.G. Gassman J. Am. Chem. Soc. 114 1992 5928 5934
11. J.A. Gerlt, and P.G. Gassman J. Am. Chem. Soc. 115 1993 11552 11568
12. J.A. Gerlt, and P.G. Gassman Biochemistry 32 1993 11943 11952
13. W.W. Cleland, P.A. Frey, and J.A. Gerlt J. Biol. Chem. 273 1998 25529 25532
14. W.W. Cleland, and M.M. Kreevoy Science 264 1994 1887 1890
15. K.S. Kim, D. Kim, J.Y. Lee, P. Tarakeshwar, and K.S. Oh Biochemistry 41 2002 5300 5306
16. J. Abildgaard, S. Bolvig, and P.E. Hansen J. Am. Chem. Soc. 120 1998 9063 9069
17. P.E. Hansen, S. Bolvig, and K. Wozniak J. Mol. Struct. 749 2005 155 168
18. H. Fuess, and H.J. Lindner Chem. Ber. 108 1975 3096 3104
19. M. Rajabi, M.Sc. thesis, University of Ferdowsi, Mashhad, Iran, 1994.
20. D. Lloyd, and N.W. Preston J. Chem. Soc. C 1969 2464 2469
21. G. Gilli, and V. Bertolasi The chemistry of enols Z. Rappoport, 1990 John Wiley and Sons N.Y.
22. M.H. Arbab Zavar, S.F. Tayyari, S. Evazmoghadam, and M. Chamsaz Asian J. Chem. 19 2007 271 282
23. S.F. Tayyari, S. Laleh, M. Zahedi-Tabrizi, and M. Vakili J. Mol. Struct. 1036 2013 151 160
24. Gaussian 09, Revision A.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
25. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
26. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
27. GaussView 5.0.8, Gaussian Inc., Garnegie Office, Park, Pittsburgh, PA 15106, USA.
28. S. Miertus, E. Scrocco, and J. Tomasi Chem. Phys. 55 1981 117 129
29. S. Miertus, and J. Tomasi Chem. Phys. 65 1982 239 245
30. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chem. Phys. Lett. 255 1996 327 335
31. J.R. Cheeseman, G.W. Trucks, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497 5509
32. K. Wolinski, J.F. Hilton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260
33. P.v.R. Schleyer, Ch. Maerker, A. Dransfeld, H. Jiao, and N.J.R. van Eikema Hommes J. Am. Chem. Soc. 118 1996 6317 6318
34. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, F. Weinhold NBO 5.0.
35. Genplot Package Computer Graphic Service, Cornel University, Utica, New York, 1990.
36. W.J. Linn, and W.H. Sharkey J. Am. Chem. Soc. 79 1957 4970 4972
37. S.F. Tayyari, Z. Moosavi-Tekyeh, M. Zahedi-Tabrizi, H. Eshghi, J.S. Emampour, H. Rahemi, and M. Hassanpour J. Mol. Struct. 782 2006 191 199
38. S.F. Tayyari, F. Naghavi, S. Pojhan, R.W. McClurg, and R.E. Sammelson J. Mol. Struct. 987 2011 241 254
39. S.F. Tayyari, F. Milani-Nejad, and H. Rahemi Spectrochim. Acta, Part A 58 2002 1669 1679
40. G. Ferguson, W.C. Marsh, R.J. Restivo, and D. Lloyd J. Chem. Soc. Perkin Trans. 2 1975 998 1004
41. S.F. Tayyari, J.S. Emampour, M. Vakili, A.R. Nekoei, H. Eshghi, S. Salemi, and M. Hassanpour J. Mol. Struct. 794 2006 204 214
42. V. Bertolasi, P. Gilli, V. Ferretti, and G. Gilli J. Am. Chem. Soc. 113 1991 4917 4925
43. S.F. Tayyari, and B. Chahkandi J. Mol. Struct. 1015 2012 74 85
44. S.F. Tayyari, and F. Milani-Nejad Spectrochim. Acta, Part A 54 1998 255 263
45. S.F. Tayyari, H. Rahemi, A.R. Nekoei, M. Zahedi-Tabrizi, and Y.A. Wang Spectrochim. Acta, Part A 66 2007 394 404
46. S.F. Tayyari, M. Zahedi-Tabrizi, H. Rahemi, H.A. Mirshahi, J.S. Emampour, M. Rajabi, and F. Milani-Nejad J. Mol. Struct. (Theochem) 730 2005 17 21
47. S.F. Tayyari, M. Zahedi-Tabrizi, F. Tayyari, and F. Milani-Nejad J. Mol. Struct. (Theochem) 637 2003 171 181
48. S.F. Tayyari, T. Bakhshi, S.J. Mahdizadeh, S. Mehrani, and R.E. Sammelson J. Mol. Struct. 938 2009 76 81
49. J. Stare, and G.G. Balint-Kurti J. Phys. Chem. A 107 2003 7204 7214
50. F. Avberlj, M. Hodoscek, and D. Hadzi Spectrochim. Acta, Part A 41 1985 89 97
51. S.F. Tayyari, and F. Milani-Nejad Spectrochim. Acta, Part A 56 2000 2679 2691
52. M. Zahedi-Tabrizi, F. Tayyari, Z. Moosavi-Tekyeh, A. Jalali, and S.F. Tayyari Spectrochim. Acta, Part A 65 2006 387 396
53. S.F. Tayyari, A.R. Nekoei, and H. Rahemi J. Mol. Struct. 882 2008 153 167