Abstract
The molecular structure of 2-(2-benzoyl-1-phenylethenyl)-5-phenylpyrrole and 2-(2-furoyl-1-phenylethenyl)-5-phenylpyrrole was studied by X-ray diffraction analysis at 110 K and quantum chemistry methods (B3LYP/6-31G*). In the crystalline state, both compounds have cyclic structures closed by strong intramolecular hydrogen bond N—H...O. Canonic zwitterionic structure contributes largely to the ground state of the molecules. This is probably due to synergism of the H-bonding and π-electron interactions.
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B. A. Trofimov, Z. V. Stepanova, L. N. Sobenina, A. I. Mikhaleva, I. A. Ushakov, and D. S. D. Toryashinova, Khim. Geterotsikl. Soedin., 1999, 1253 [Chem. Heterocycl. Compd., 1999 (Engl. Transl.)].
N. N. Chipanina, Z. V. Stepanova, G. A. Gavrilova, L. N. Sobenina, and A. I. Mikhaleva, Izv. Akad. Nauk, Ser. Khim., 2000, 1945 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1914].
G. C. Pimentel and A. L. McClellan, The Hydrogen Bond, W. H. Freeman, San Francisco-London, 1960, 440 pp.
T. Dziembowska, Pol. J. Chem., 1994, 1455.
G. Gilli, F. Bellucci, V. Ferretti, and V. Bertolasi, J. Am. Chem. Soc., 1989, 111, 1023.
D. N. Shigorin, Dokl. Akad. Nauk SSSR [Dokl. Chem.], 1956, 108, 672 (in Russian).
D. N. Shigorin, in Vodorodnaya svyaz´ [The Hydrogen Bond], Nauka, Moscow, 1964, 195 (in Russian).
V. Bertolasi, V. Ferretti, P. Gilli, G. Gilli, Y. M. Issa, and O. E. Sherif, J. Chem. Soc., Perkin Trans. 2, 1993, 2223.
V. Bertolasi, P. Gilli, V. Ferretti, and G. Gilli, Acta Crystallogr., Sect. B., 1994, 50, 617.
T. M. Krigowski, K. Wozniak, R. Anulewicz, D. Pawlak, W. Kolodziejski, E.Grech, and A. Szady, J. Phys. Chem., 1997, 101, 9399.
P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 1994, 116, 909.
V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, and K. Vaughan, New J. Chem., 1999, 23, 1261.
A. I. Kitaigorodskii, P. M. Zorkii, and V. K. Bel´skii, in Stroenie organicheskogo veshchestva. Dannye strukturnykh issledovanii. 1971-1973 [The Structure of Organic Matter. Structural Analysis Data. 1971-1973], Nauka, Moscow, 1982, 511 (in Russian).
Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 1995, 64, 446 [Russ. Chem. Rev., 1995, 64 (Engl. Transl.)].
K. Ohkura, S. Kashino, and M. Haisa, Bull. Chem. Soc. Jpn., 1973, 46, 627.
L. G. Vorontsova and G. S. Kazaryan, Zh. Strukt. Khim., 1973, 14, 1089 [J. Struct. Chem., 1973, 14 (Engl. Transl.)].
P. V. Huong and G. Noel, Spectrochim. Acta, 1976, 32A, 831.
SMART V5.0 and SAINT V5.0, Area Detector Control and Integration Software, 1998, Bruker AXS, Inc., Madison (WI), USA.
G. M. Sheldrick, SADABS, 1999, Bruker AXS, Inc., Madison (WI), USA.
G. M. Sheldrick, SHELXTL NT V5.10, 1999, Bruker AXS, Inc., Madison (WI), USA.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98, Revision A.6, Gaussian, Inc., Pittsburgh (PA), 1998.
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Chipanina, N.N., Turchaninov, V.K., Vorontsov, I.I. et al. Strong intramolecular hydrogen bond N—H...O in 2-(2-acyl-1-phenylethenyl)-5-phenylpyrroles. Russian Chemical Bulletin 51, 111–116 (2002). https://doi.org/10.1023/A:1015069915668
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DOI: https://doi.org/10.1023/A:1015069915668