Electron-withdrawing effects on the molecular structure of 2- and 3-nitrobenzonitrile revealed by broadband microwave spectroscopy
Graneek, Jack B.
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https://hdl.handle.net/2142/100569
Description
Title
Electron-withdrawing effects on the molecular structure of 2- and 3-nitrobenzonitrile revealed by broadband microwave spectroscopy
Author(s)
Graneek, Jack B.
Contributor(s)
Schnell, Melanie
Issue Date
2018-06-18
Keyword(s)
Structure determination
Abstract
Nitrobenzonitrile consists of two electron-withdrawing groups, which have negative inductive and mesomeric effects on the phenyl ring resulting in interesting physical properties. The rotational spectra of 2- and 3-nitrobenzonitrile were recorded via chirped-pulse Fourier transform microwave spectroscopy in the frequency range of 2−8 GHz. For both molecules, the main isotopologues and all isotopologues of the respective 13C-, 15N-, 18O-monosubstituted species in their natural abundance were assigned. These assignments allowed for the structural determination of 2- and 3-nitrobenzonitrile via Kraitchman’s equations as well as a mass-dependent least-squares fitting approach. Structural changes caused by steric interaction and competition for the electron density of the phenyl ring highlight how these strong electron-withdrawing substituents affect one another according to their respective positions on the phenyl ring.
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