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Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study
Author(s) -
Yang Dapeng,
Yang Guang,
Zhao Jinfeng,
Song Nahong,
Zheng Rui,
Wang Yusheng
Publication year - 2018
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3729
Subject(s) - chemistry , intramolecular force , isoquinoline , quinoline , photochemistry , excited state , cyclohexane , acetonitrile , computational chemistry , proton , hydrogen bond , potential energy surface , solvent , polar , solvent effects , ab initio , organic chemistry , molecule , atomic physics , astronomy , physics , quantum mechanics
In this present work, we theoretically study the excited state intramolecular proton transfer (ESIPT) mechanism about a quinoline/isoquinoline‐pyrazole isomer QP‐I system. Compared with previous experimental results, our calculated results reappear previous data, which further confirm the theoretical level we used is reasonable. We mainly adopt 2 kinds of solvents (nonpolar cyclohexane and polar acetonitrile) to explore solvents effects on this system. Through reduced density gradient (RDG) function, the intramolecular hydrogen bond N1─H2···N3 has been confirmed existing in both S 0 and S 1 states, although the distance between H2 and N3 is not short. In addition, the strengthening N1─H2···N3 in the S 1 state provides possibility for ESIPT. Explorations about charge redistribution reveal the trend of ESIPT, and frontier orbital gap reflects the reactivity in polar and nonpolar solvents. The constructing potential energy curves reveal that potential energy barriers could be controlled and regulated by solvent polarity.