Structural distortion of the epoxy groups in norbornanes: a rotational study of exo-2,3-epoxynorbornane

Patricia Écija; Iciar Uriarte; Francisco J Basterretxea; Judith Millán; Alberto Lesarri; José A Fernández; Emilio J Cocinero

doi:10.1002/cphc.201500334

Structural distortion of the epoxy groups in norbornanes: a rotational study of exo-2,3-epoxynorbornane

Chemphyschem. 2015 Aug 24;16(12):2609-14. doi: 10.1002/cphc.201500334. Epub 2015 Jul 16.

Authors

Patricia Écija¹, Iciar Uriarte¹, Francisco J Basterretxea¹, Judith Millán², Alberto Lesarri³, José A Fernández¹, Emilio J Cocinero⁴

Affiliations

¹ Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco (UPV-EHU), Apartado 644, 48080 Bilbao (Spain)http://grupodeespectroscopia.es/MW/
² Departamento de Química, Facultad de Ciencias, Estudios Agroalimentarios e Informática, Universidad de La Rioja, 26006 Logroño (Spain).
³ Departamento de Química Física y Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, 47011 Valladolid (Spain).
⁴ Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco (UPV-EHU), Apartado 644, 48080 Bilbao (Spain)http://grupodeespectroscopia.es/MW/. emiliojose.cocinero@ehu.es.

PMID: 26182910
DOI: 10.1002/cphc.201500334

Abstract

Exo-2,3-epoxynorbornane is studied in the gas phase by pulsed jet Fourier transform microwave spectroscopy in the 4-18 GHz region. Six isotopologues were observed and characterized in their natural abundance. The experimental substitution and effective structures were obtained. Comparison with the structure of norbornane shows significant differences in several bond lengths and valence angles upon introduction of the epoxy group. All the work is supported by quantum chemical calculations.

Keywords: bridged bicyclic rings; isotopes; microwave spectroscopy; rotational spectroscopy; structure elucidation.