Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

Hetmańczyk, Łukasz; Goremychkin, Eugene A.; Waliszewski, Janusz; Vener, Mikhail V.; Lipkowski, Paweł; Tolstoy, Peter M.; Filarowski, Aleksander

doi:10.3390/molecules26165043

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Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

Łukasz Hetmańczyk

Eugene A. Goremychkin

²,

³,

^4,5

⁶

^7,*

and

Aleksander Filarowski

^2,8,*

Faculty of Chemistry, Jagiellonian University, 2 Gronostajowa Str., 30-387 Cracow, Poland

Frank Laboratory of Neutron Physics, Joint Institute for Nuclear Research 6 F. Joliot-Curie str., 141980 Dubna, Russia

Faculty of Physics, University of Bialystok, 1L Ciolkowskiego str., 15-245 Bialystok, Poland

⁴

Quantum Chemistry Department, Mendeleev University of Chemical Technology, Miusskaya Square 9, 125047 Moscow, Russia

⁵

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia

⁶

Department of Physical and Quantum Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańnskiego 27, 50-370 Wrocław, Poland

⁷

Institute of Chemistry, St. Petersburg State University, Universitetskij pr. 26, 198504 Saint Petersburg, Russia

⁸

Faculty of Chemistry, University of Wrocław 14 F. Joliot-Curie str., 50-383 Wrocław, Poland

Authors to whom correspondence should be addressed.

Academic Editor: Mirosław Jabłoński

Molecules 2021, 26(16), 5043; https://doi.org/10.3390/molecules26165043

Received: 31 July 2021 / Revised: 13 August 2021 / Accepted: 16 August 2021 / Published: 20 August 2021

(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2021)

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Abstract

The ortho-hydroxy aryl Schiff base 2-[(E)-(phenylimino)methyl]phenol and its deutero-derivative have been studied by the inelastic incoherent neutron scattering (IINS), infrared (IR) and Raman experimental methods, as well as by Density Functional Theory (DFT) and Density-Functional Perturbation Theory (DFPT) simulations. The assignments of vibrational modes within the 3500–50 cm⁻¹ spectral region made it possible to state that the strong hydrogen bond in the studied compound can be classified as the so-called quasi-aromatic bond. The isotopic substitution supplemented by the results of DFT calculations allowed us to identify vibrational bands associated with all five major hydrogen bond vibrations. Quasi-isostructural polymorphism of 2-[(E)-(phenylimino)methyl]phenol (SA) and 2-[(E)-(phenyl-D₅-imino)methyl]phenol (SA-C₆D₅) has been studied by powder X-ray diffraction in the 20–320 K temperature range. View Full-Text

Keywords: Schiff bases; inelastic incoherent neutron scattering; hydrogen bond; isotopic effect

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Hetmańczyk, Ł.; Goremychkin, E.A.; Waliszewski, J.; Vener, M.V.; Lipkowski, P.; Tolstoy, P.M.; Filarowski, A. Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline. Molecules 2021, 26, 5043. https://doi.org/10.3390/molecules26165043

AMA Style

Hetmańczyk Ł, Goremychkin EA, Waliszewski J, Vener MV, Lipkowski P, Tolstoy PM, Filarowski A. Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline. Molecules. 2021; 26(16):5043. https://doi.org/10.3390/molecules26165043

Chicago/Turabian Style

Hetmańczyk, Łukasz, Eugene A. Goremychkin, Janusz Waliszewski, Mikhail V. Vener, Paweł Lipkowski, Peter M. Tolstoy, and Aleksander Filarowski. 2021. "Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline" Molecules 26, no. 16: 5043. https://doi.org/10.3390/molecules26165043

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