Počet záznamů: 1  

Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives

  1. 1. 0477164 - UOCHB-X 2018 RIV US eng J - Článek v odborném periodiku
    Zborowski, K. K. - Szatylowicz, H. - Stasyuk, Olga A. - Krygowski, T. M.
    Towards physical interpretation of substituent effects: the case of N- and C3-substituted pyrrole derivatives.
    Structural Chemistry. Roč. 28, č. 4 (2017), s. 1223-1227 ISSN 1040-0400
    Institucionální podpora: RVO:61388963
    Klíčová slova: substituent effect * pyrrole derivatives * Hammett equation * charges of the substituent active region
    Kód oboru RIV: CF - Fyzikální chemie a teoretická chemie
    Obor OECD: Physical chemistry
    Impakt faktor: 2.019, rok: 2017
    https://link.springer.com/article/10.1007%2Fs11224-017-0938-7

    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.
    Trvalý link: http://hdl.handle.net/11104/0273546