Issue 44, 2022

The many forms of alpha-methoxy phenylacetic acid in the gas phase: flexibility, internal dynamics, and their intramolecular interactions

Abstract

We present a rotational spectroscopy study of alpha-methoxy phenylacetic acid in the gas phase. This acid is a derivative of mandelic acid and is used in various organic reactions. The conformational landscape of alpha-methoxy phenylacetic acid was explored to gain insight into its intramolecular dynamics. A rich rotational spectrum was obtained using chirped-pulse Fourier transform microwave spectroscopy in the 2–8 GHz range. Five conformers out of six calculated low-energy forms were identified in the spectrum, and the assignment of the 13C singly substituted isotopologues for the lowest-energy conformer led to its accurate structure determination. Splitting patterns were analyzed and attributed to the internal rotation of a methyl top. The analysis of the non-covalent interactions within the molecule highlights the subtle balance in the stabilization of the different conformers. We thus provide high-level structural and intramolecular dynamics information that is also used to benchmark the performance of quantum-chemical calculations.

Graphical abstract: The many forms of alpha-methoxy phenylacetic acid in the gas phase: flexibility, internal dynamics, and their intramolecular interactions

Supplementary files

Article information

Article type
Paper
Submitted
26 авг 2022
Accepted
17 окт 2022
First published
19 окт 2022

Phys. Chem. Chem. Phys., 2022,24, 27312-27320

The many forms of alpha-methoxy phenylacetic acid in the gas phase: flexibility, internal dynamics, and their intramolecular interactions

H. Singh, P. Pinacho, D. A. Obenchain, M. M. Quesada-Moreno and M. Schnell, Phys. Chem. Chem. Phys., 2022, 24, 27312 DOI: 10.1039/D2CP03962A

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