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Infrared spectra of nitrostyrene derivatives

✍ Scribed by R.E. Clavijo; R. Araya-Maturana; B.K. Cassels; B. Weiss-López

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
743 KB
Volume
50
Category
Article
ISSN
1386-1425

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✦ Synopsis

The IR spectra of a series of 6 phenylnitroethenes (PNE) and 6 phenylnitropropenes (PNP) were assigned, based on a normal coordinates calculation performed on styrene and styrene-d,. Some frequencies were sensitive to the electronic properties of the substituents, and others to the substitution on C@. AM1 minimum energy conformations and rotational barriers around the Cl-Ca bond were calculated. According to these calculations, PNE are planar and PNP display an angle of 45" between the ethylenic and aromatic planes. AMI underestimates the height of the electronic barriers, which is however modulated by the electron donor properties of the substituent on the ring. A correlation between the calculated electronic barrier and the C=C ethylenic stretching frequency was observed.

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