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Volumn 133, Issue 10, 2011, Pages 3381-3389

Erratum: Stabilities of carbenes: Independent measures for singlets and triplets (Journal of the American Chemical Society (2011) 133 (3381-3389) DOI: 10.1021/ja1071493);Stabilities of carbenes: Independent measures for singlets and triplets

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY; HYDROGENATION; STABILIZATION;

EID: 79952588842     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204721f     Document Type: Erratum
Times cited : (89)

References (89)
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    • A discussion of electronic effects on ground state triplet carbenes is given by Nemirowski, A.; Schreiner, P. R. J. Org. Chem. 2007, 72, 9533
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    • This criterion was applied to several N-heterocyclic carbenes, silylenes, and germylenes by Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039
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    • Gaussian, Inc., Pittsburgh, PA,. All structures reported here represent electronic energy minima except for structures identified as transition states, each of which has one imaginary frequency.
    • Frisch, M. J., et al. GAUSSIAN 03, Revision B.04; Gaussian, Inc., Pittsburgh, PA, 2003. All structures reported here represent electronic energy minima except for structures identified as transition states, each of which has one imaginary frequency.
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    • and references therein Recent studies include the following: J. Am. Chem. Soc. 2002, 124, 6428 (in which the solvent dependence of proton transfer to singlet diphenylcarbene was studied)
    • For earlier studies see Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770 and references therein Recent studies include the following: Peon, J.; Polshakov, D.; Kohler, B. J. Am. Chem. Soc. 2002, 124, 6428 (in which the solvent dependence of proton transfer to singlet diphenylcarbene was studied)
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    • (a study of the photochemistry of a diazo ester and a diazo ketone)
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    • (a study of proton transfer from water to singlet chloro-, fluoro-, and cyanocarbenes by computation)
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    • Carbenes (special issue)
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    • Editorial
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    • Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
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    • Unless otherwise noted, experimental values were taken or calculated from data given by Bartmess, J. E. In NIST Standard Reference Database Number 69; Mallard, W. G.; Linstrom, P. J., Eds.; http://webbook.nist.gov; National Institute of Standards and Technology, Gaithersburg, MD, 2003.
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    • and references therein
    • 2 symmetry; see Seburg, R. A.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 2009, 131, 9442 and references therein. In both cases, our calculated geometrical parameters are in good agreement with those of the McMahon group
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    • + system; see, for example, Saunders, M.; Jiménez-Vásquez, H. A. Stable Carbocation Chemistry; Prakash, G. K. S.; Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1997; Chapt. 9, pp 304 - 306.
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    • Kassaee, M. Z.; Ghambarian, M.; Musavi, S. M.; Shakib, F. A.; Momeni, M. R. J. Phys. Org. Chem. 2009, 22, 919. These authors studied cyclic three-membered carbenes, saturated and unsaturated, containing a variety of heteroatoms; they found NICS(0) = -16.8 for cyclopropenylidene). There is a large early literature for this carbene. See, for example, refs 22b-22g
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  • 55
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    • See ref 1i. Values are based on electronic energies, without zero-point vibrational energy or thermal corrections.
    • See ref 1i. Values are based on electronic energies, without zero-point vibrational energy or thermal corrections.
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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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    • Singlet dinitrocarbene has been studied computationally as a reagent for cycloaddition to carbon nanostructures: Lee, Y.-S.; Marzari, N. J. Phys. Chem. C 2008, 112, 4480
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    • Others have used isodesmic processes to evaluate carbene stabilization energies for limited sets of carbenes. Values obtained by Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770 are in reasonable agreement with ours
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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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    • references therein
    • Seburg, R. A.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 2009, 131, 9442 and references therein. Note our disclaimer concerning spin contamination in the triplet of this species.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9442
    • Seburg, R.A.1    Patterson, E.V.2    McMahon, R.J.3
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    • and also ref 2
    • 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.
    • Bertrand and co-workers (7) calculate their highly substituted abnormal NHC to be 14.1 kcal/mol less stable than its normal NHC isomer.
  • 84
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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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    • Bernasconi, C.F.1    Wenzel, P.J.2    Ragains, M.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.