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Synthesis, crystal structure and electron density analysis of a sulfanyl 2-pyridone analogue: Tautomeric preference and conformation locking by S···O chalcogen bonding

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Synthesis, crystal structure and electron density analysis of a sulfanyl 2-pyridone analogue : Tautomeric preference and conformation locking by S···O chalcogen bonding. / Menon, Prasanth K.; Krishnaraj, K. U.; Anabha, E. R.; Devaky, K. S.; Thomas, Sajesh P.

I: Journal of Molecular Structure, Bind 1222, 128798, 12.2020.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avisTidsskriftartikelForskningpeer review

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Menon, Prasanth K. ; Krishnaraj, K. U. ; Anabha, E. R. ; Devaky, K. S. ; Thomas, Sajesh P. / Synthesis, crystal structure and electron density analysis of a sulfanyl 2-pyridone analogue : Tautomeric preference and conformation locking by S···O chalcogen bonding. I: Journal of Molecular Structure. 2020 ; Bind 1222.

Bibtex

@article{1a0cc2c6fcb5412c8a8bfd2ce3cdab1d,
title = "Synthesis, crystal structure and electron density analysis of a sulfanyl 2-pyridone analogue: Tautomeric preference and conformation locking by S···O chalcogen bonding",
abstract = "The effect of intra-molecular chalcogen bonding involving S(sp3)···O(sp2) interaction in locking the molecular conformation has been investigated in 2-hydroxy-5-(4-methoxybenzoyl)-6-(methylsulfanyl)nicotinonitrile. The compound has been synthesized in a one-pot synthetic method and structurally characterized by NMR, FT-IR spectroscopic techniques and single crystal X-ray diffraction. The strength and n→σ∗ nature of the S···O interaction have been revealed by electron density topological analysis and second order perturbation energy estimation of orbital interaction. Among the two possible tautomers, the molecule prefers the relatively less stable one in the solid-state. A rare but robust hydroxyl-nitrile supramolecular synthon identified in the structure helps to understand this tautomeric preference.",
keywords = "CHARGE-DENSITY, DRUG-RECEPTOR INTERACTIONS, ENERGY FRAMEWORKS, FENOBAM, INSIGHTS, INTERMOLECULAR INTERACTIONS, MODEL ENERGIES, POLYMORPHISM, PROGRESS",
author = "Menon, {Prasanth K.} and Krishnaraj, {K. U.} and Anabha, {E. R.} and Devaky, {K. S.} and Thomas, {Sajesh P.}",
year = "2020",
month = dec,
doi = "10.1016/j.molstruc.2020.128798",
language = "English",
volume = "1222",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis, crystal structure and electron density analysis of a sulfanyl 2-pyridone analogue

T2 - Tautomeric preference and conformation locking by S···O chalcogen bonding

AU - Menon, Prasanth K.

AU - Krishnaraj, K. U.

AU - Anabha, E. R.

AU - Devaky, K. S.

AU - Thomas, Sajesh P.

PY - 2020/12

Y1 - 2020/12

N2 - The effect of intra-molecular chalcogen bonding involving S(sp3)···O(sp2) interaction in locking the molecular conformation has been investigated in 2-hydroxy-5-(4-methoxybenzoyl)-6-(methylsulfanyl)nicotinonitrile. The compound has been synthesized in a one-pot synthetic method and structurally characterized by NMR, FT-IR spectroscopic techniques and single crystal X-ray diffraction. The strength and n→σ∗ nature of the S···O interaction have been revealed by electron density topological analysis and second order perturbation energy estimation of orbital interaction. Among the two possible tautomers, the molecule prefers the relatively less stable one in the solid-state. A rare but robust hydroxyl-nitrile supramolecular synthon identified in the structure helps to understand this tautomeric preference.

AB - The effect of intra-molecular chalcogen bonding involving S(sp3)···O(sp2) interaction in locking the molecular conformation has been investigated in 2-hydroxy-5-(4-methoxybenzoyl)-6-(methylsulfanyl)nicotinonitrile. The compound has been synthesized in a one-pot synthetic method and structurally characterized by NMR, FT-IR spectroscopic techniques and single crystal X-ray diffraction. The strength and n→σ∗ nature of the S···O interaction have been revealed by electron density topological analysis and second order perturbation energy estimation of orbital interaction. Among the two possible tautomers, the molecule prefers the relatively less stable one in the solid-state. A rare but robust hydroxyl-nitrile supramolecular synthon identified in the structure helps to understand this tautomeric preference.

KW - CHARGE-DENSITY

KW - DRUG-RECEPTOR INTERACTIONS

KW - ENERGY FRAMEWORKS

KW - FENOBAM

KW - INSIGHTS

KW - INTERMOLECULAR INTERACTIONS

KW - MODEL ENERGIES

KW - POLYMORPHISM

KW - PROGRESS

UR - http://www.scopus.com/inward/record.url?scp=85087876499&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2020.128798

DO - 10.1016/j.molstruc.2020.128798

M3 - Journal article

AN - SCOPUS:85087876499

VL - 1222

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

M1 - 128798

ER -