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Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives
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SYSNO ASEP 0477164 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives Tvůrce(i) Zborowski, K. K. (PL)
Szatylowicz, H. (PL)
Stasyuk, Olga A. (UOCHB-X)
Krygowski, T. M. (PL)Zdroj.dok. Structural Chemistry. - : SPRINGER/PLENUM PUBLISHERS - ISSN 1040-0400
Roč. 28, č. 4 (2017), s. 1223-1227Poč.str. 5 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova substituent effect ; pyrrole derivatives ; Hammett equation ; charges of the substituent active region Vědní obor RIV CF - Fyzikální chemie a teoretická chemie Obor OECD Physical chemistry Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000404241800028 EID SCOPUS 85014752744 DOI 10.1007/s11224-017-0938-7 Anotace Classical and reverse substituent effects were studied for pyrrole derivatives. Two extensive sets of pyrrole derivatives with NO, NO2, CN, CF3, COMe, COOH, CHO, CONH2, Cl, SH, SiH3, F, PH2, H, Me, OMe, OH, NH2, NHMe, NMe2, Li, BeH, BH2, Na, MgH, and AlH2 substituents at N and C3 positions were taken into account. Analysis of the substituent effects was based on charges of the Substituent Active Region (cSAR). The cSAR values were obtained from atomic charges calculated within the Quantum Theory of Atoms in Molecules (QTAIM) methodology. Calculations were performed at the B3LYP/6-311++G** level of theory. It was documented that classical substituent effect in substituted pyrroles is much greater (approximately ten times) for substituents at C3 position than at NH group. The reverse substituent effect is also greater in C3-substituted pyrroles that in N-substituted ones. As a result of observed correlations, substituent constants for some rare substituents such as Li, BeH, BH2, Na, MgH, and AlH2 were evaluated. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2018 Elektronická adresa https://link.springer.com/article/10.1007%2Fs11224-017-0938-7
Počet záznamů: 1