The nature of conformational preference in a number of p-alkyl phenols and p-alkyl benzenes

Literature Information

Publication Date 2002-09-13
DOI 10.1039/B203954K
Impact Factor 3.676
Authors

Patricia R. Richardson, Madelaine A. Chapman, Daniel C. Wilson, Simon P. Bates, Anita C. Jones


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Abstract

The energy barriers to hydroxyl rotation and alkyl rotation in p-cresol, p-isopropylphenol, p-tert-butylphenol, isopropylbenzene and tert-butylbenzene have been calculated using the MP2/6-31g(d,p) model chemistry. The number of stable conformers predicted for isopropylbenzene, tert-butylbenzene, p-isopropylphenol and p-tert-butylphenol is consistent with experimental observations. The doubling of stable alkyl conformation, and hence spectral features, in the p-alkyl phenols is due to syn and anti orientations of the hydroxyl and alkyl substituents and can be related to an asymmetry in the electron density in the HOMO of phenol. Hyperconjugation is found to have an important influence on the torsional potential of the alkyl substituent.

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Contents list

Front/Back Matter

DOI: 10.1039/C7CP90228J

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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