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Volumn 28, Issue 2, 2015, Pages 147-162

Orbital hybridization: A key electronic factor in control of structure and reactivity

Author keywords

Bent's rule; Conjugation hyperconjugation; Hybridization; Reactivity structure; Rehybridization Copyright

Indexed keywords

CHEMISTRY; PHYSICAL CHEMISTRY;

EID: 84922912279     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.3382     Document Type: Review
Times cited : (118)

References (124)
  • 3
    • 84922909935 scopus 로고    scopus 로고
    • The percentage of s-character and the hybridization parameter λ are linked through the two equivalent equations: 100 / (λ + 1) = %s and %p/λ=%s
    • The percentage of s-character and the hybridization parameter λ are linked through the two equivalent equations: 100 / (λ + 1) = %s and %p/λ=%s.
  • 13
    • 79960053089 scopus 로고    scopus 로고
    • a) A. Grushow, J. Chem. Ed. 2011, 88(7), 860-862
    • (2011) J. Chem. Ed. , vol.88 , Issue.7 , pp. 860-862
    • Grushow, A.1
  • 14
  • 16
    • 84861563498 scopus 로고    scopus 로고
    • b) N. J. Tro, J. Chem. Ed. 2012, 89(5), 567
    • (2012) J. Chem. Ed. , vol.89 , Issue.5 , pp. 567
    • Tro, N.J.1
  • 30
    • 84922909932 scopus 로고    scopus 로고
    • An interesting potential consequence of the increased s-character in the N-H bonds is their increased acidity and potential to form stronger H bonds and be better solvated in suitable solvents
    • An interesting potential consequence of the increased s-character in the N-H bonds is their increased acidity and potential to form stronger H bonds and be better solvated in suitable solvents.
  • 32
    • 84922909931 scopus 로고    scopus 로고
    • ref. 4
    • a) ref. 4.
  • 46
    • 84922909928 scopus 로고    scopus 로고
    • Selected rehybridization examples
    • Selected rehybridization examples.
  • 78
    • 84884244503 scopus 로고    scopus 로고
    • (For detailed analysis of electronic and structural effects in this and related reactions, see: a) Unusual reactivity in cycloaromatization reactions
    • (For detailed analysis of electronic and structural effects in this and related reactions, see: a) R. K. Mohamed, P. W. Peterson, I. V. Alabugin, Chem. Rev. 2013, 113, 7089; Unusual reactivity in cycloaromatization reactions:
    • (2013) Chem. Rev. , vol.113 , pp. 7089
    • Mohamed, R.K.1    Peterson, P.W.2    Alabugin, I.V.3
  • 81
    • 84962348617 scopus 로고    scopus 로고
    • Hybridization is not the only accelerating factor in these systems. Hyperconjugation and H.F interactions play important roles as well
    • Hybridization is not the only accelerating factor in these systems. Hyperconjugation and H.F interactions play important roles as well: a) B. Gold, N. E. Shevchenko, N. Bonus, G. B. Dudley, I. V. Alabugin, J. Org. Chem. 2012, 77, 75
    • (2012) J. Org. Chem. , vol.77 , pp. 75
    • Gold, B.1    Shevchenko, N.E.2    Bonus, N.3    Dudley, G.B.4    Alabugin, I.V.5
  • 85
    • 84922909922 scopus 로고    scopus 로고
    • This model was suggested by Professor Wes Borden
    • This model was suggested by Professor Wes Borden.
  • 100
  • 114
    • 84922909920 scopus 로고    scopus 로고
    • F. W. Weinhold, private communication
    • F. W. Weinhold, private communication.
  • 115
    • 36049049423 scopus 로고    scopus 로고
    • Ammonia borane is interesting as a potential compound for hydrogen storage
    • Ammonia borane is interesting as a potential compound for hydrogen storage: a) T. B. Marder, Angew. Chem. Int. Ed. 2007, 46, 8116
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8116
    • Marder, T.B.1
  • 120
    • 85051836241 scopus 로고    scopus 로고
    • Furthermore, the ~2.5° deviation of the bond-forming orbitals from the line connecting N and H also contributes to the unusual values for the HNH angles
    • Furthermore, the ~2.5° deviation of the bond-forming orbitals from the line connecting N and H also contributes to the unusual values for the HNH angles.
  • 121
    • 84922909916 scopus 로고    scopus 로고
    • Hyperconjugative effects also play a role, especially in closely matched situations
    • Hyperconjugative effects also play a role, especially in closely matched situations.
  • 122
    • 1942521263 scopus 로고    scopus 로고
    • For creative use of unusual aziridine reactivity, see
    • For creative use of unusual aziridine reactivity, see: a) I. D. G. Watson, S. A. Styler, A. K. Yudin, J. Am. Chem. Soc. 2004, 126, 5086
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5086
    • Watson, I.D.G.1    Styler, S.A.2    Yudin, A.K.3
  • 124
    • 84914109473 scopus 로고    scopus 로고
    • For a very interesting recent report of dramatic changes in acidity as a consequence of altered hybridization in the process of bond angle change, see
    • For a very interesting recent report of dramatic changes in acidity as a consequence of altered hybridization in the process of bond angle change, see: Y. Mo, B. M. Ahmed, L. Guan, J. Karty, G. Mezei, Org. Lett. 2014, 16, 4680-4683.
    • (2014) Org. Lett. , vol.16 , pp. 4680-4683
    • Mo, Y.1    Ahmed, B.M.2    Guan, L.3    Karty, J.4    Mezei, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.