Phenol-Quinone Tautomerism in (Arylazo)naphthols and the Analogous Schiff Bases: Benchmark Calculations

被引：22

作者：

Ali, S. Tahir ^{[1
,3
]}

Antonov, Liudmil ^{[2
]}

Fabian, Walter M. F. ^{[3
]}

机构：

[1] Fed Urdu Univ Arts Sci & Technol, Dept Chem, Karachi, Sindh, Pakistan

[2] Bulgarian Acad Sci, Ctr Phytochem, Inst Organ Chem, BU-1113 Sofia, Bulgaria

[3] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2014年 / 118卷 / 04期

关键词：

MOLECULAR-ORBITAL METHODS; MAIN-GROUP THERMOCHEMISTRY; GAUSSIAN-BASIS SETS; DENSITY FUNCTIONALS; PROTON-TRANSFER; NONCOVALENT INTERACTIONS; FREE-ENERGIES; MODEL; EQUILIBRIUM; ACCURATE;

D O I：

10.1021/jp411502u

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Tautomerization energies of a series of isomeric [(4-R-phenyl)azo]-naphthols and the analogous Schiff bases (R = N(CH3)(2), OCH3, H, CN, NO2) are calculated by LPNO-CEPA/1-CBS using the def2-TZVPP and def2-QZVPP basis sets for extrapolation. The performance of various density functionals (B3LYP, M06-2X, PW6B95, B2PLYP, mPW2PLYP, PWPB95) as well as MP2 and SCS-MP2 is evaluated against these results. M06-2X and SCS-MP2 yield results close to the LPNO-CEPA/1-CBS values. Solvent effects (CCl4, CHCl3, CH3CN, and CH3OH) are treated by a variety of bulk solvation models (SM8, IEFPCM, COSMO, PBF, and SMD) as well as explicit solvation (Monte Carlo free energy perturbation using the OPLSAA force field).

引用

页码：778 / 789

页数：12

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