Competition between In-Plane vs Above-Plane Configurations of Water with Aromatic Molecules: Non-Covalent Interactions in 1,4-Naphthoquinone-(H2O)1-3Complexes

Shefali Baweja, Sanjana Panchagnula, M. Eugenia Sanz*, Luca Evangelisti, Cristóbal Pérez, Channing West, Brooks H. Pate

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Non-covalent interactions between aromatic molecules and water are fundamental in many chemical and biological processes, and their accurate description is essential to understand molecular relative configurations. Here we present the rotational spectroscopy study of the water complexes of the polycyclic aromatic hydrocarbon 1,4-naphthoquinone (1,4-NQ). In 1,4-NQ-(H2O)1,2, water molecules bind through O-H···O and C-H···O hydrogen bonds and are located on the plane of 1,4-NQ. For 1,4-NQ-(H2O)3, in-plane and above-plane water configurations are observed exhibiting O-H···O, C-H···O, and lone pair···π-hole interactions. The observation of different water arrangements for 1,4-NQ-(H2O)3 allows benchmarking theoretical methods and shows that they have great difficulty in predicting energy orderings due to the strong competition of C-H···O binding with πand π-hole interactions. This study provides important insight into water interactions with aromatic systems and the challenges in their modeling.

Original languageEnglish
Pages (from-to)9510-9516
Number of pages7
JournalJournal of physical chemistry letters
Volume13
Issue number40
DOIs
Publication statusPublished - 13 Oct 2022

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