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See ref 1i. Values are based on electronic energies, without zero-point vibrational energy or thermal corrections.
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A structure for the singlet, obtained by Orrego, J. F.; Cano, H.; Restrep, A. J. Phys. Chem. A 2009, 113, 6517, is likewise very similar to ours
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s structure at HF/6-31G* with the nitro group perpendicular to the CH moiety. However, it rearranges at MP2/6-31G* by a 1,2-oxygen migration from nitrogen to carbon, yielding " nitrosocarbaldehyde". See also Tao, Y.; Ding, Y.; Li, Z.; Huang, X.; Sun, C.-C. J. Phys. Chem. A 2001, 105, 3388
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Those obtained by Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647 agree well with ours for first-row substituents but not so well with second-row substituents Nemirowski and Schreiner (1i) report results for diaminocarbene, giving a value for CSE(triplet) in very good agreement with ours, but their CSE(singlet) value is some 35 kcal/mol smaller than ours. Freeman (1k) used isodesmic processes to evaluate resonance stabilization of vinylcarbene.
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A recent review of aromaticity criteria, including the NICS method, is given by Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842
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Important earlier work addressing the issue of aromaticity in imidazol-2-ylidene and related species was reported by Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023 and also ref 2
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Bertrand and co-workers (7) calculate their highly substituted abnormal NHC to be 14.1 kcal/mol less stable than its normal NHC isomer.
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Bertrand and co-workers (7) calculate their highly substituted abnormal NHC to be 14.1 kcal/mol less stable than its normal NHC isomer.
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83
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Kudavalli, J. S.; Boyd, D. R.; Coyne, D.; Keeffe, J. R.; Lawlor, D. A.; MacCormac, A. C.; More O'Ferrall, R. A.; Rao, S. N.; Sharma, N. D. Org. Lett. 2010, 12, 555
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Geometric evidence indicates the interaction resembles that in the cyclobutenyl cation, described as homoaromatic. In both species the calculated transannular C1-C3 distances are very small, 1.788 Å in the carbene and 1.736 Å for the cation; compare those in singlet vinylcarbene and allyl cation (2.291 and 2.365 Å, respectively). This enables a significant bonding C1-C3 interaction in the cyclic systems. For discussion and leading references to homoaromaticity in cyclobutenyl cation, see Bernasconi, C. F.; Wenzel, P J.; Ragains, M. L. J. Am. Chem. Soc. 2008, 130, 4934
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See also Sieber, S.; Schleyer, P. v. R.; Otto, A. H.; Gauss, J.; Reichel, F.; Cremer, D. J. Phys. Org. Chem. 1993, 6, 445
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