Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

Marta Pérez-Torralba; Concepción López; Carlos Pérez-Medina; Rosa M. Claramunt; Elena Pinilla; M. Rosario Torres; Ibon Alkorta; José Elguero

doi:10.1039/c0ce00249f

Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

Marta Pérez-Torralba
, Concepción López
, Carlos Pérez-Medina
, Rosa M. Claramunt
, Elena Pinilla
, M. Rosario Torres
, Ibon Alkorta
, José Elguero

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

8 Scopus citations

Abstract

The neutral dimer formed by 4,6-difluoro-1H,2H-indazolin-3-one and 3-hydroxy-4,6-difluoro-1H-indazole linked by two hydrogen bonds presents a very fast intermolecular double proton transfer in the solid state (ISSPT). The combined use of crystallography, solid state NMR and DFT [B3LYP/6-311++G(d,p)] calculations supports this interesting observation and allows us to estimate a barrier of about 20 kJ mol^-1.

Original language	English
Pages (from-to)	4052-4055
Number of pages	4
Journal	CrystEngComm
Volume	12
Issue number	12
DOIs	https://doi.org/10.1039/c0ce00249f
State	Published - Dec 2010
Externally published	Yes

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title = "Fast degenerate double proton transfer in the solid state between two indazolinone tautomers",

abstract = "The neutral dimer formed by 4,6-difluoro-1H,2H-indazolin-3-one and 3-hydroxy-4,6-difluoro-1H-indazole linked by two hydrogen bonds presents a very fast intermolecular double proton transfer in the solid state (ISSPT). The combined use of crystallography, solid state NMR and DFT [B3LYP/6-311++G(d,p)] calculations supports this interesting observation and allows us to estimate a barrier of about 20 kJ mol-1.",

author = "Marta P{\'e}rez-Torralba and Concepci{\'o}n L{\'o}pez and Carlos P{\'e}rez-Medina and Claramunt, \{Rosa M.\} and Elena Pinilla and Torres, \{M. Rosario\} and Ibon Alkorta and Jos{\'e} Elguero",

year = "2010",

month = dec,

doi = "10.1039/c0ce00249f",

language = "English",

volume = "12",

pages = "4052--4055",

journal = "CrystEngComm",

issn = "1466-8033",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

AU - Pérez-Torralba, Marta

AU - López, Concepción

AU - Pérez-Medina, Carlos

AU - Claramunt, Rosa M.

AU - Pinilla, Elena

AU - Torres, M. Rosario

AU - Alkorta, Ibon

AU - Elguero, José

PY - 2010/12

Y1 - 2010/12

N2 - The neutral dimer formed by 4,6-difluoro-1H,2H-indazolin-3-one and 3-hydroxy-4,6-difluoro-1H-indazole linked by two hydrogen bonds presents a very fast intermolecular double proton transfer in the solid state (ISSPT). The combined use of crystallography, solid state NMR and DFT [B3LYP/6-311++G(d,p)] calculations supports this interesting observation and allows us to estimate a barrier of about 20 kJ mol-1.

AB - The neutral dimer formed by 4,6-difluoro-1H,2H-indazolin-3-one and 3-hydroxy-4,6-difluoro-1H-indazole linked by two hydrogen bonds presents a very fast intermolecular double proton transfer in the solid state (ISSPT). The combined use of crystallography, solid state NMR and DFT [B3LYP/6-311++G(d,p)] calculations supports this interesting observation and allows us to estimate a barrier of about 20 kJ mol-1.

UR - https://www.scopus.com/pages/publications/78349232020

U2 - 10.1039/c0ce00249f

DO - 10.1039/c0ce00249f

M3 - Article

AN - SCOPUS:78349232020

SN - 1466-8033

VL - 12

SP - 4052

EP - 4055

JO - CrystEngComm

JF - CrystEngComm

IS - 12

ER -

Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

Abstract

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