Theoretical study of the thermolysis reaction of β-hydroxynitriles in the gas phase

The gas‐phase thermal decomposition of 3‐hydroxypropionitrile, 3‐hydroxybutyronitrile, and 3‐hydroxy‐3‐methylbutyronitrile has been studied at the MP2/6‐31G(d) level of theory at 683.15 K and 0.06 atm. Results based both in energy and structure data seem to indicate a favorable route of decompositio...

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Bibliographic Details
Published in:International journal of quantum chemistry 2003, Vol.91 (5), p.618-625
Main Authors: Chamorro, Eduardo, Quijano, Jairo, Notario, Rafael, Sánchez, Claudia, León, Luis A., Chuchani, Gabriel
Format: Article
Language:English
Subjects:
ab initio computational methods
reaction mechanisms
thermolysis reactions
transition-state structures
β-hydroxynitriles
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Summary:The gas‐phase thermal decomposition of 3‐hydroxypropionitrile, 3‐hydroxybutyronitrile, and 3‐hydroxy‐3‐methylbutyronitrile has been studied at the MP2/6‐31G(d) level of theory at 683.15 K and 0.06 atm. Results based both in energy and structure data seem to indicate a favorable route of decomposition via a six‐membered cyclic transition state (similar to those suggested for thermal decomposition of other related compounds, such as β‐hydroxyketones, β‐hydroxyalkenes, and β‐hydroxyalkynes) rather than a four‐membered cyclic transition state or even a quasiheterolytic pathway. © 2003 Wiley Periodicals, Inc. Int J Quantum Chem, 2003
ISSN:0020-7608
1097-461X
DOI:10.1002/qua.10469