Comparative Structural Study of Three Tetrahalophthalic Anhydrides: Recognition of X···O(anhydride) Halogen Bond and πh···O(anhydride) Interaction.

Sergey V Baykov, Artem V Semenov, Eugene A Katlenok, Anton A Shetnev, Nadezhda A Bokach

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Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors at 3 institutions in 1 country.

Sergey V BaykovInstitute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, Russia.ORCID 0000-0002-8912-5816

Artem V SemenovM.V. Lomonosov Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadskogo Pr, 119571 Moscow, Russia.

Eugene A KatlenokInstitute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, Russia.ORCID 0000-0002-4485-7247

Anton A ShetnevPharmaceutical Technology Transfer Centre, Yaroslavl State Pedagogical University Named after K.D. Ushinsky, 108 Respublikanskaya St., 150000 Yaroslavl, Russia.ORCID 0000-0002-4389-461X

Nadezhda A BokachInstitute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, Russia.ORCID 0000-0001-8692-9627

St Petersburg University · RUInstitute of Bioorganic Chemistry · RUYaroslavl State Pedagogical University · RU

Funding

Council for Grants of the President of Russian Federation MK-1074.2020.3

6 · The paper itself

Abstract

Structures of three tetrahalophthalic anhydrides (TXPA: halogen = Cl (TCPA), Br (TBPA), I (TIPA)) were studied by X-ray diffraction, and several types of halogen bonds (HaB) and lone pair···π-hole (lp···πh) contacts were revealed in their structures. HaBs involving the central oxygen atom of anhydride group (further X···O(anhydride) were recognized in the structures of TCPA and TBPA. In contrast, for the O(anhydride) atom of TIPA, only interactions with the π system (π-hole) of the anhydride ring (further lp(O)···πh) were observed. Computational studies by a number of theoretical methods (molecular electrostatic potentials, the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital analyses, the electron density difference, and symmetry-adapted perturbation theory) demonstrated that the X···O(anhydride) contacts in TCPA and TBPA and lp(O)···πh in TIPA are caused by the packing effect. The supramolecular architecture of isostructural TCPA and TBPA was mainly affected by X···O(acyl) and X···X HaBs, and, for TIPA, the main contribution provided I···I HaBs.

Indexed as

computational studieshalogen bondnoncovalent interactionstetrahalophthalic anhydridesX-ray diffraction studies

Identifiers

PMID34071107

DOI10.3390/molecules26113119

PMCPMC8197102

OpenAlexW3165519739

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LicenceCC BY

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