Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone

Santiago Mata; Vanessa Cortijo; W. Caminati; Jose L. Alonso; Maria Eugenia Sanz; Juan C. Lopez; Susana Blanco

doi:10.1021/jp104625z

Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone

Santiago Mata, Vanessa Cortijo, W. Caminati, Jose L. Alonso^*, Maria Eugenia Sanz, Juan C. Lopez, Susana Blanco

^*Corresponding author for this work

Chemistry

Universidad de Valladolid

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

The Fourier transform microwave spectra of the hydrated forms of the tautomeric pair 2-pyridinone/2-hydroxypyridine (2PO/2HP) have been investigated in a supersonic expansion. Three hydrated species, 2PO-H(2)O, 2HP-H(2)O, and 2PO-(H(2)O)(2), have been observed in the rotational spectrum. Each molecular complex was confidently identified by the features of the (14)N quadrupole hyperfine structure of the rotational transitions. The presence of water affects the tautomeric equilibrium -N=C(OH)- -NH-C(=O)-, which is shifted to the enol form for the bare molecules 2PO/2HP but to the keto tautomer for the hydrated forms.

Original language	English
Pages (from-to)	11393-11398
Number of pages	6
Journal	JOURNAL OF PHYSICAL CHEMISTRY A
Volume	114
Issue number	43
DOIs	https://doi.org/10.1021/jp104625z
Publication status	Published - 4 Nov 2010

Keywords

GAS-PHASE
MICROWAVE-SPECTRUM
PROTON-TRANSFER
ROTATIONAL SPECTROSCOPY
INFRARED-SPECTRA
2-PYRIDONE
WATER
CLUSTERS
URACIL
EQUILIBRIUM

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@article{ca558ed023a6450f9d085c9199e22dcd,

title = "Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone",

abstract = "The Fourier transform microwave spectra of the hydrated forms of the tautomeric pair 2-pyridinone/2-hydroxypyridine (2PO/2HP) have been investigated in a supersonic expansion. Three hydrated species, 2PO-H(2)O, 2HP-H(2)O, and 2PO-(H(2)O)(2), have been observed in the rotational spectrum. Each molecular complex was confidently identified by the features of the (14)N quadrupole hyperfine structure of the rotational transitions. The presence of water affects the tautomeric equilibrium -N=C(OH)- -NH-C(=O)-, which is shifted to the enol form for the bare molecules 2PO/2HP but to the keto tautomer for the hydrated forms.",

keywords = "GAS-PHASE, MICROWAVE-SPECTRUM, PROTON-TRANSFER, ROTATIONAL SPECTROSCOPY, INFRARED-SPECTRA, 2-PYRIDONE, WATER, CLUSTERS, URACIL, EQUILIBRIUM",

author = "Santiago Mata and Vanessa Cortijo and W. Caminati and Alonso, {Jose L.} and Sanz, {Maria Eugenia} and Lopez, {Juan C.} and Susana Blanco",

year = "2010",

month = nov,

day = "4",

doi = "10.1021/jp104625z",

language = "English",

volume = "114",

pages = "11393--11398",

journal = "JOURNAL OF PHYSICAL CHEMISTRY A",

issn = "1089-5639",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone

AU - Mata, Santiago

AU - Cortijo, Vanessa

AU - Caminati, W.

AU - Alonso, Jose L.

AU - Sanz, Maria Eugenia

AU - Lopez, Juan C.

AU - Blanco, Susana

PY - 2010/11/4

Y1 - 2010/11/4

N2 - The Fourier transform microwave spectra of the hydrated forms of the tautomeric pair 2-pyridinone/2-hydroxypyridine (2PO/2HP) have been investigated in a supersonic expansion. Three hydrated species, 2PO-H(2)O, 2HP-H(2)O, and 2PO-(H(2)O)(2), have been observed in the rotational spectrum. Each molecular complex was confidently identified by the features of the (14)N quadrupole hyperfine structure of the rotational transitions. The presence of water affects the tautomeric equilibrium -N=C(OH)- -NH-C(=O)-, which is shifted to the enol form for the bare molecules 2PO/2HP but to the keto tautomer for the hydrated forms.

AB - The Fourier transform microwave spectra of the hydrated forms of the tautomeric pair 2-pyridinone/2-hydroxypyridine (2PO/2HP) have been investigated in a supersonic expansion. Three hydrated species, 2PO-H(2)O, 2HP-H(2)O, and 2PO-(H(2)O)(2), have been observed in the rotational spectrum. Each molecular complex was confidently identified by the features of the (14)N quadrupole hyperfine structure of the rotational transitions. The presence of water affects the tautomeric equilibrium -N=C(OH)- -NH-C(=O)-, which is shifted to the enol form for the bare molecules 2PO/2HP but to the keto tautomer for the hydrated forms.

KW - GAS-PHASE

KW - MICROWAVE-SPECTRUM

KW - PROTON-TRANSFER

KW - ROTATIONAL SPECTROSCOPY

KW - INFRARED-SPECTRA

KW - 2-PYRIDONE

KW - WATER

KW - CLUSTERS

KW - URACIL

KW - EQUILIBRIUM

U2 - 10.1021/jp104625z

DO - 10.1021/jp104625z

M3 - Article

SN - 1089-5639

VL - 114

SP - 11393

EP - 11398

JO - JOURNAL OF PHYSICAL CHEMISTRY A

JF - JOURNAL OF PHYSICAL CHEMISTRY A

IS - 43

ER -

Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone

Abstract

Keywords

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