1997
DOI: 10.1021/ja9729342
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Experimental Confirmation of the Iminocyclohexadienyl Cation-like Structure of Arylnitrenium Ions:  Time-Resolved IR Studies of Diphenylnitrenium Ion

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Cited by 66 publications
(149 citation statements)
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“…[66] These short CÀN bonds and the alternation of the C À C bond lengths in the phenyl rings observed for the 2-fluorenylnitrene species indicates both the singlet and triplet states have significant iminocyclohexadienyl character, although to a varying extent. This behavior is similar to that found for several arylnitrenium ions [48,56,60] including the 2-fluorenylnitrenium ion. [60] Symmetric aromatic CC stretch vibrational modes in the 1568 ± 1628 cm À1 region were previously found to correlate with the degree of iminocyclohexadienyl character of several arylnitrenium ions.…”
Section: Resultssupporting
confidence: 86%
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“…[66] These short CÀN bonds and the alternation of the C À C bond lengths in the phenyl rings observed for the 2-fluorenylnitrene species indicates both the singlet and triplet states have significant iminocyclohexadienyl character, although to a varying extent. This behavior is similar to that found for several arylnitrenium ions [48,56,60] including the 2-fluorenylnitrenium ion. [60] Symmetric aromatic CC stretch vibrational modes in the 1568 ± 1628 cm À1 region were previously found to correlate with the degree of iminocyclohexadienyl character of several arylnitrenium ions.…”
Section: Resultssupporting
confidence: 86%
“…Several studies have used a comparison of vibrational frequencies computed with density functional to experimental frequencies observed in either time-resolved Raman or IR spectra to convincingly assign several different arylnitrenium ions to their singlet ground states, [48,56,60] and we expect a similar approach may be useful for arylnitrene species. We have performed UBPW91/cc-PVDZ calculations to find the optimized geometry and predicted vibrational frequencies for the singlet and triplet 2-fluorenylnitrene species.…”
Section: Resultsmentioning
confidence: 92%
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“…32 No experimental IR data have yet been reported for primary aryl nitrenium ions. However, Toscano and coworkers 33 …”
Section: N C Nmentioning
confidence: 98%
“…Nevertheless, it is significant that it was observed at a higher frequency than the analogous vibration in diphenylamine. 33 Because of their generally smaller size, alkyl nitrenium ions have been studied at far higher levels of DFT and ab initio theory than is currently possible for many of the systems considered here Ž 34 . see, e.g., Gonzales et al .…”
Section: N C Nmentioning
confidence: 99%