caa a22 4500 475760522 CHVBK 20180406123549.0 cr unu---uuuuu 170329e20001001xx s 000 0 eng 10.1007/BF02496335 doi (NATIONALLICENCE)springer-10.1007/BF02496335 Quantum-chemical study of the protonation of pyrrolo[2,1- b ]thiazole and its selenium and tellurium analogs [Elektronische Daten] [V. Shagun, L. Sinegovskaya, D. Toryashinova, A. Mal'kina, L. Brandsma, B. Trofimov] The possibility of proton attack on various centers in pyrrolo[2,1-b]thiazole (1) has been evaluated. The results of semiempirical (MNDO, AM1, and PM3) andab initio (6-31G*) calculations were compared. The MNDO and 6-31G* methods give "chemically proper” and qualitatively coincident results. Analysis of the intramolecular (geometric and electronic) reorganization of molecule1, depending on the protonation center, has been carried out. The most probable attack centers, depending on the mechanism of electrophilic reaction, have been recognized. The energy parameters of intramolecular prototropic rearrangements in cation1 and the "blocking” factor value of methyl groups reducting the corresponding complex stability have been evaluated. It has been established that the relative stability of the protonated forms does not change on going to pyrrolo[2,1-b]selenium- and telluriumazoles, but the range of variations is considerably narrowed in the series S>Se>Te. Kluwer Academic/Plenum Publishers, 2000 pyrrolothiazole nationallicence protonation nationallicence quantum-chemical calculation nationallicence orbital control nationallicence transition states nationallicence Shagun V. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut Sinegovskaya L. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut Toryashinova D. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut Mal'kina A. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut Brandsma L. Department of Preparative Organic Chemistry, University of Utrecht, Padualaan 8, 3584 CH, Utrecht, The Netherlands aut Trofimov B. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/10(2000-10-01), 1691-1695 1066-5285 49:10<1691 2000 49 11172 https://doi.org/10.1007/BF02496335 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02496335 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Shagun V. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut NATIONALLICENCE 700 1- Sinegovskaya L. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut NATIONALLICENCE 700 1- Toryashinova D. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut NATIONALLICENCE 700 1- Mal'kina A. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut NATIONALLICENCE 700 1- Brandsma L. Department of Preparative Organic Chemistry, University of Utrecht, Padualaan 8, 3584 CH, Utrecht, The Netherlands aut NATIONALLICENCE 700 1- Trofimov B. Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/10(2000-10-01), 1691-1695 1066-5285 49:10<1691 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer