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Volumn 118, Issue 20, 2014, Pages 3663-3677

Hybridization trends for main group elements and expanding the Bent's rule beyond carbon: More than electronegativity

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; POLARIZATION;

EID: 84901279395     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp502472u     Document Type: Article
Times cited : (88)

References (88)
  • 1
    • 33947340154 scopus 로고
    • The nature of the chemical bond. Application of results obtained from the quantum mechanics and from a theory of paramagnetic susceptibility to the structure of molecules
    • Pauling, L. The nature of the chemical bond. Application of results obtained from the quantum mechanics and from a theory of paramagnetic susceptibility to the structure of molecules J. Am. Chem. Soc. 1931, 53, 1367-1400
    • (1931) J. Am. Chem. Soc. , vol.53 , pp. 1367-1400
    • Pauling, L.1
  • 3
    • 0024845170 scopus 로고
    • Electronegativity is the average one-electron energy of the valence-shell electrons in ground-state free atoms
    • Allen, L. C. Electronegativity is the average one-electron energy of the valence-shell electrons in ground-state free atoms J. Am. Chem. Soc. 1989, 111, 9003-9014
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9003-9014
    • Allen, L.C.1
  • 4
    • 0034733128 scopus 로고    scopus 로고
    • C-H interactions, anomeric effect what is really important?
    • C-H interactions, anomeric effect what is really important? J. Org. Chem. 2000, 65, 3910-3919
    • (2000) J. Org. Chem. , vol.65 , pp. 3910-3919
    • Alabugin, I.V.1
  • 5
    • 79960053089 scopus 로고    scopus 로고
    • Is it time to retire the hybrid atomic orbital?
    • Grushow, A. Is it time to retire the hybrid atomic orbital? J. Chem. Educ. 2011, 88 (7) 860-862
    • (2011) J. Chem. Educ. , vol.88 , Issue.7 , pp. 860-862
    • Grushow, A.1
  • 6
    • 84861550723 scopus 로고    scopus 로고
    • In response to those who wish to retain hybrid atomic orbitals in the curriculum
    • Grushow, A. In response to those who wish to retain hybrid atomic orbitals in the curriculum J. Chem. Educ. 2012, 89 (5) 578
    • (2012) J. Chem. Educ. , vol.89 , Issue.5 , pp. 578
    • Grushow, A.1
  • 7
    • 84861537342 scopus 로고    scopus 로고
    • In defense of the hybrid atomic orbitals
    • Hiberty, P. C.; Volatron, F.; Shaik, S. In defense of the hybrid atomic orbitals J. Chem. Educ. 2012, 89, 575-577
    • (2012) J. Chem. Educ. , vol.89 , pp. 575-577
    • Hiberty, P.C.1    Volatron, F.2    Shaik, S.3
  • 8
    • 84861563498 scopus 로고    scopus 로고
    • Retire the hybrid atomic orbital? Not so fast
    • Tro, N. J. Retire the hybrid atomic orbital? Not so fast J. Chem. Educ. 2012, 89, 567-568
    • (2012) J. Chem. Educ. , vol.89 , pp. 567-568
    • Tro, N.J.1
  • 9
    • 84861548243 scopus 로고    scopus 로고
    • Retire hybrid atomic orbitals?
    • DeKock, R. L. Retire hybrid atomic orbitals? J. Chem. Educ. 2012, 89 (5) 569-569
    • (2012) J. Chem. Educ. , vol.89 , Issue.5 , pp. 569-569
    • Dekock, R.L.1
  • 10
    • 84861563192 scopus 로고    scopus 로고
    • Comments on "is it time to retire the hybrid atomic orbital?
    • Landis, C. R.; Weinhold, F. Comments on "Is it time to retire the hybrid atomic orbital? J. Chem. Educ. 2012, 89, 570-572
    • (2012) J. Chem. Educ. , vol.89 , pp. 570-572
    • Landis, C.R.1    Weinhold, F.2
  • 11
    • 0037957336 scopus 로고    scopus 로고
    • The electronic basis of improper hydrogen bonding: A subtle balance of hyperconjugation and rehybridization
    • Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. The electronic basis of improper hydrogen bonding: A subtle balance of hyperconjugation and rehybridization J. Am. Chem. Soc. 2003, 125, 5973-5987
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 5973-5987
    • Alabugin, I.V.1    Manoharan, M.2    Peabody, S.3    Weinhold, F.4
  • 12
    • 33846606944 scopus 로고    scopus 로고
    • Rehybridization as a general mechanism for maximizing chemical and supramolecular bonding and a driving force for chemical reactions
    • Alabugin, I. V.; Manoharan, M. Rehybridization as a general mechanism for maximizing chemical and supramolecular bonding and a driving force for chemical reactions J. Comput. Chem. 2007, 28, 373-390
    • (2007) J. Comput. Chem. , vol.28 , pp. 373-390
    • Alabugin, I.V.1    Manoharan, M.2
  • 13
    • 84867706279 scopus 로고    scopus 로고
    • Racing carbon atoms. Atomic motion reaction coordinates and structural effects on newtonian kinetic isotope effects
    • Andujar-De Sanctis, I. L.; Singleton, D. A. Racing carbon atoms. atomic motion reaction coordinates and structural effects on newtonian kinetic isotope effects Org. Lett. 2012, 14, 5238-5241
    • (2012) Org. Lett. , vol.14 , pp. 5238-5241
    • Andujar-De Sanctis, I.L.1    Singleton, D.A.2
  • 14
    • 67650530548 scopus 로고    scopus 로고
    • Newtonian kinetic isotope effects. Observation, prediction, and origin of heavy-atom dynamic isotope effects
    • Kelly, K. K.; Hirschi, J. S.; Singleton, D. A. Newtonian kinetic isotope effects. observation, prediction, and origin of heavy-atom dynamic isotope effects J. Am. Chem. Soc. 2009, 131, 8382-8383
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 8382-8383
    • Kelly, K.K.1    Hirschi, J.S.2    Singleton, D.A.3
  • 15
    • 84867948517 scopus 로고    scopus 로고
    • Imbalanced tunneling ready states in alcohol dehydrogenase model reactions: Rehybridization lags behind H-tunneling
    • Hammann, B.; Razzaghi, M.; Kashefolgheta, S.; Lu, Y. Imbalanced tunneling ready states in alcohol dehydrogenase model reactions: Rehybridization lags behind H-tunneling Chem. Commun. 2012, 48, 11337-11339
    • (2012) Chem. Commun. , vol.48 , pp. 11337-11339
    • Hammann, B.1    Razzaghi, M.2    Kashefolgheta, S.3    Lu, Y.4
  • 16
    • 80051596304 scopus 로고    scopus 로고
    • 2)benzylamine: Nitrogen rehybridization and CH bond cleavage are not concerted
    • 2)benzylamine: Nitrogen rehybridization and CH bond cleavage are not concerted J. Am. Chem. Soc. 2011, 133, 12319-12321
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 12319-12321
    • MacMillar, S.1    Edmondson, D.E.2    Matsson, O.3
  • 18
    • 0342409779 scopus 로고
    • Distribution of atomic s character in molecules and its chemical implications
    • Bent, H. A. Distribution of atomic s character in molecules and its chemical implications J. Chem. Educ. 1960, 37, 616-624
    • (1960) J. Chem. Educ. , vol.37 , pp. 616-624
    • Bent, H.A.1
  • 19
    • 33947479158 scopus 로고
    • An appraisal of valence-bond structures and hybridization in compounds of the first-row elements
    • Bent, H. A. An appraisal of valence-bond structures and hybridization in compounds of the first-row elements Chem. Rev. 1961, 61, 275-311
    • (1961) Chem. Rev. , vol.61 , pp. 275-311
    • Bent, H.A.1
  • 20
    • 0001040872 scopus 로고
    • Some generalizations concerning the reactivity of aryl positions adjacent to fused strained rings
    • Streitwieser, A.; Ziegler, G. R.; Mowey, P. C.; Lewis, A.; Lawler, R. G. Some generalizations concerning the reactivity of aryl positions adjacent to fused strained rings J. Am. Chem. Soc. 1968, 90, 1357-1358
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1357-1358
    • Streitwieser, A.1    Ziegler, G.R.2    Mowey, P.C.3    Lewis, A.4    Lawler, R.G.5
  • 21
    • 33845282697 scopus 로고
    • Rehybridization and.pi.-orbital overlap in nonplanar conjugated organic molecules:.pi.-orbital axis vector (POAV) analysis and three-dimensional Hueckel molecular orbital (3D-HMO) theory
    • Haddon, R. C. Rehybridization and.pi.-orbital overlap in nonplanar conjugated organic molecules:.pi.-orbital axis vector (POAV) analysis and three-dimensional Hueckel molecular orbital (3D-HMO) theory J. Am. Chem. Soc. 1987, 109, 1676-1685
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1676-1685
    • Haddon, R.C.1
  • 22
    • 33845280325 scopus 로고
    • Transferability of natural bond orbitals
    • Carpenter, J. E.; Weinhold, F. Transferability of natural bond orbitals J. Am. Chem. Soc. 1988, 110, 368-372
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 368-372
    • Carpenter, J.E.1    Weinhold, F.2
  • 23
    • 0001713444 scopus 로고
    • B initio study of.sigma.- and.pi.-effects in benzenes fused to four-membered rings: Rehybridization, delocalization, and antiaromaticity
    • Faust, R.; Glendening, E. D.; Streitwieser, A.; Vollhardt, P. C. b initio study of.sigma.- and.pi.-effects in benzenes fused to four-membered rings: Rehybridization, delocalization, and antiaromaticity J. Am. Chem. Soc. 1992, 114, 8263-8268
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8263-8268
    • Faust, R.1    Glendening, E.D.2    Streitwieser, A.3    Vollhardt, P.C.4
  • 24
    • 28444447058 scopus 로고    scopus 로고
    • Solvent polarization and kinetic isotope effects in nitroethane deprotonation and implications to the nitroalkane oxidase reaction
    • Major, D. T.; York, D. M.; Gao, J. Solvent polarization and kinetic isotope effects in nitroethane deprotonation and implications to the nitroalkane oxidase reaction J. Am. Chem. Soc. 2005, 127, 16374-16375
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 16374-16375
    • Major, D.T.1    York, D.M.2    Gao, J.3
  • 25
    • 0001365878 scopus 로고    scopus 로고
    • Delocalization in allyl cation, radical, and anion
    • Mo, Y.; Lin, Z.; Wu, W.; Zhang, Q. Delocalization in allyl cation, radical, and anion J. Phys. Chem. 1996, 100 (16) 6469-6474
    • (1996) J. Phys. Chem. , vol.100 , Issue.16 , pp. 6469-6474
    • Mo, Y.1    Lin, Z.2    Wu, W.3    Zhang, Q.4
  • 27
    • 0030295776 scopus 로고    scopus 로고
    • Molecular and electronic structure of 1,2-disilacyclobutabenzenes. Ab initio molecular orbital and density functional study
    • Eckert-Maksić; Glasovac, Z.; Hodošček, M.; Lesar, A.; Maksić, Z. B. Molecular and electronic structure of 1,2-disilacyclobutabenzenes. Ab initio molecular orbital and density functional study J. Organomet. Chem. 1996, 524 (1-2) 107-114
    • (1996) J. Organomet. Chem. , vol.524 , Issue.1-2 , pp. 107-114
    • Eckert-Maksić1    Glasovac, Z.2    Hodošček, M.3    Lesar, A.4    Maksić, Z.B.5
  • 28
    • 15844401781 scopus 로고    scopus 로고
    • Hydrogenation of weakly rehybridized ethylene on Fe(100)-h: Ethyl group formation
    • Merrill, P. B.; Madix, R. J. Hydrogenation of weakly rehybridized ethylene on Fe(100)-h: ethyl group formation J. Am. Chem. Soc. 1996, 118, 5062-5067
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5062-5067
    • Merrill, P.B.1    Madix, R.J.2
  • 29
    • 0000492996 scopus 로고    scopus 로고
    • Density functional theory and perturbation calculations on some lewis acid-base complexes. A systematic study of substitution effects
    • Skancke, A.; Skancke, P. N. Density functional theory and perturbation calculations on some lewis acid-base complexes. A systematic study of substitution effects J. Phys. Chem. 1996, 100, 15079-15082
    • (1996) J. Phys. Chem. , vol.100 , pp. 15079-15082
    • Skancke, A.1    Skancke, P.N.2
  • 30
    • 0000436545 scopus 로고    scopus 로고
    • Density functional calculations of the influence of substitution on singlet-triplet gaps in carbenes and vinylidenes
    • Worthington, S. E.; Cramer, C. J. Density functional calculations of the influence of substitution on singlet-triplet gaps in carbenes and vinylidenes J. Phys. Org. Chem. 1997, 10, 755-757
    • (1997) J. Phys. Org. Chem. , vol.10 , pp. 755-757
    • Worthington, S.E.1    Cramer, C.J.2
  • 31
    • 0031002206 scopus 로고    scopus 로고
    • 2 studied by SCF and MP2 localised orbital calculations
    • 2 studied by SCF and MP2 localised orbital calculations J. Mol. Struct. 1997, 405, 193-205
    • (1997) J. Mol. Struct. , vol.405 , pp. 193-205
    • Palmer, M.H.1
  • 32
    • 30244470429 scopus 로고    scopus 로고
    • Rehybridization in annelated benzene and dissociating glyoxal
    • Ou, M. C.; Chu, S. Y. Rehybridization in annelated benzene and dissociating glyoxal J. Mol. Struct. (Theochem) 1997, 401, 87-92
    • (1997) J. Mol. Struct. (Theochem) , vol.401 , pp. 87-92
    • Ou, M.C.1    Chu, S.Y.2
  • 33
    • 0035925131 scopus 로고    scopus 로고
    • 13C NMR spectroscopy and computational studies
    • 13C NMR spectroscopy and computational studies J. Am. Chem. Soc. 2001, 123, 1327-1336
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1327-1336
    • Lewis, B.E.1    Schramm, V.L.2
  • 34
    • 0037071716 scopus 로고    scopus 로고
    • Planarization of 1,3,5,7-cyclooctatetraene as a result of a partial rehybridization at carbon atoms: An MP2/6-31G* and B3LYP/6- 311G** study
    • Krygowski, T. M.; Pindelska, E.; Cryański, M. K.; Häfelinger, G. Planarization of 1,3,5,7-cyclooctatetraene as a result of a partial rehybridization at carbon atoms: An MP2/6-31G* and B3LYP/6- 311G** study Chem. Phys. Lett. 2002, 359, 158-162
    • (2002) Chem. Phys. Lett. , vol.359 , pp. 158-162
    • Krygowski, T.M.1    Pindelska, E.2    Cryański, M.K.3    Häfelinger, G.4
  • 35
    • 0037129513 scopus 로고    scopus 로고
    • Rehybridized 1,3-butadiene radical cations: How far will a radical cation go to maintain conjugation?
    • Oxgaard, J.; Wiest, O. Rehybridized 1,3-butadiene radical cations: How far will a radical cation go to maintain conjugation? J. Phys. Chem. A 2002, 106, 3967-3974
    • (2002) J. Phys. Chem. A , vol.106 , pp. 3967-3974
    • Oxgaard, J.1    Wiest, O.2
  • 36
    • 0037094089 scopus 로고    scopus 로고
    • Directing power of cyclobutenoid annelations on the double bonds of planar cyclooctatetraenes
    • Baldridge, K. K.; Siegel, J. S. Directing power of cyclobutenoid annelations on the double bonds of planar cyclooctatetraenes J. Am. Chem. Soc. 2002, 124, 5514-5517
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5514-5517
    • Baldridge, K.K.1    Siegel, J.S.2
  • 38
    • 0037414551 scopus 로고    scopus 로고
    • P -Benzyne derivatives that have exceptionally small singlet-triplet gaps and even a triplet ground state
    • Clark, A. E.; Davidson, E. R. p -Benzyne derivatives that have exceptionally small singlet-triplet gaps and even a triplet ground state J. Org. Chem. 2003, 68, 3387-3396
    • (2003) J. Org. Chem. , vol.68 , pp. 3387-3396
    • Clark, A.E.1    Davidson, E.R.2
  • 39
    • 0242582498 scopus 로고    scopus 로고
    • Homoanomeric effects in six-membered heterocycles
    • Alabugin, I. V.; Manoharan, M.; Zeidan, T. A. Homoanomeric effects in six-membered heterocycles J. Am. Chem. Soc. 2003, 125, 14014-14031
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14014-14031
    • Alabugin, I.V.1    Manoharan, M.2    Zeidan, T.A.3
  • 41
    • 23144440526 scopus 로고    scopus 로고
    • A DFT study of the amination of fullerenes and carbon nanotubes: Reactivity and curvature
    • Lin, T.; Zhang, W. D.; Huang, J.; He, C. A DFT study of the amination of fullerenes and carbon nanotubes: Reactivity and curvature J. Phys. Chem. B 2005, 109, 13755-13760
    • (2005) J. Phys. Chem. B , vol.109 , pp. 13755-13760
    • Lin, T.1    Zhang, W.D.2    Huang, J.3    He, C.4
  • 42
    • 0242414459 scopus 로고    scopus 로고
    • Effect of metal complexation on ring opening of bowl-shaped hydrocarbons: Theoretical study
    • In clusters
    • In clusters: Jemmis, E. D.; Parameswaran, P.; Anoop, A. Effect of metal complexation on ring opening of bowl-shaped hydrocarbons: Theoretical study Int. J. Quantum Chem. 2003, 95, 810-815
    • (2003) Int. J. Quantum Chem. , vol.95 , pp. 810-815
    • Jemmis, E.D.1    Parameswaran, P.2    Anoop, A.3
  • 43
    • 27144461162 scopus 로고    scopus 로고
    • Nonperfect synchronization of reaction center rehybridization in the transition state of the hydride transfer catalyzed by dihydrofolate reductase
    • Pu, J.; Ma, S.; Garcia-Viloca, M.; Gao, J.; Truhlar, D. G.; Kohen, A. Nonperfect synchronization of reaction center rehybridization in the transition state of the hydride transfer catalyzed by dihydrofolate reductase J. Am. Chem. Soc. 2005, 127, 14879-14886
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14879-14886
    • Pu, J.1    Ma, S.2    Garcia-Viloca, M.3    Gao, J.4    Truhlar, D.G.5    Kohen, A.6
  • 44
    • 0035861045 scopus 로고    scopus 로고
    • Effect of rehybridization on the electronic structure of single-walled carbon nanotubes
    • Hamon, M. A.; Itkis, M. E.; Alvaraez, T.; Kuper, C.; Menon, M.; Haddon, R. C. Effect of rehybridization on the electronic structure of single-walled carbon nanotubes J. Am. Chem. Soc. 2001, 123, 11292-11293
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11292-11293
    • Hamon, M.A.1    Itkis, M.E.2    Alvaraez, T.3    Kuper, C.4    Menon, M.5    Haddon, R.C.6
  • 45
    • 0032569202 scopus 로고    scopus 로고
    • Synergism of catalysis and reaction center rehybridization. An ab initio study of the hydrolysis of the parent carbodiimide
    • In reactions
    • In reactions: Lewis, M.; Glaser, R. Synergism of catalysis and reaction center rehybridization. An ab initio study of the hydrolysis of the parent carbodiimide J. Am. Chem. Soc. 1998, 120, 8541-8542
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8541-8542
    • Lewis, M.1    Glaser, R.2
  • 46
    • 0141682803 scopus 로고    scopus 로고
    • Synergism of catalysis and reaction center rehybridization. A novel mode of catalysis in the hydrolysis of carbon dioxide
    • Lewis, M.; Glaser, R. Synergism of catalysis and reaction center rehybridization. A novel mode of catalysis in the hydrolysis of carbon dioxide J. Phys. Chem. A 2003, 107, 6814-6818
    • (2003) J. Phys. Chem. A , vol.107 , pp. 6814-6818
    • Lewis, M.1    Glaser, R.2
  • 48
    • 84884244503 scopus 로고    scopus 로고
    • Concerted reactions that produce diradicals and zwitterions: Electronic, steric, conformational, and kinetic control of cycloaromatization processes
    • Mohamed, R. K.; Peterson, P. W.; Alabugin, I. V. Concerted reactions that produce diradicals and zwitterions: Electronic, steric, conformational, and kinetic control of cycloaromatization processes Chem. Rev. 2013, 113, 7089-7112
    • (2013) Chem. Rev. , vol.113 , pp. 7089-7112
    • Mohamed, R.K.1    Peterson, P.W.2    Alabugin, I.V.3
  • 49
    • 84962385193 scopus 로고    scopus 로고
    • Moderating strain without sacrificing reactivity: Design of fast and tunable noncatalyzed alkyne-azide cycloadditions via stereoelectronically controlled transition state stabilization
    • Gold, B.; Dudley, G. B.; Alabugin, I. V. Moderating strain without sacrificing reactivity: Design of fast and tunable noncatalyzed alkyne-azide cycloadditions via stereoelectronically controlled transition state stabilization J. Am. Chem. Soc. 2013, 135, 1558
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 1558
    • Gold, B.1    Dudley, G.B.2    Alabugin, I.V.3
  • 50
    • 84882369119 scopus 로고    scopus 로고
    • Two functional groups in one package": Designing cascade transformations of alkynes.
    • "Two functional groups in one package": Designing cascade transformations of alkynes. Alabugin, I. V.; Gold, B. J. Org. Chem. 2013, 78, 7777-7784
    • (2013) J. Org. Chem. , vol.78 , pp. 7777-7784
    • Alabugin, I.V.1    Gold, B.2
  • 51
    • 38149016915 scopus 로고    scopus 로고
    • Understanding Organofluorine Chemistry. An Introduction to the C-F Bond
    • For a particularly instructive selection of rehybridization effects in reactivity of fluoroorganic compounds, see
    • For a particularly instructive selection of rehybridization effects in reactivity of fluoroorganic compounds, see: O'Hagan, D. Understanding Organofluorine Chemistry. An Introduction to the C-F Bond Chem. Soc. Rev. 2008, 37, 308-319
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 308-319
    • O'Hagan, D.1
  • 53
    • 2142672995 scopus 로고
    • Bent's rule: Energetics, electronegativity, and the structures of nonmetal fluorides
    • Huheey, J. E. Bent's rule: Energetics, electronegativity, and the structures of nonmetal fluorides Inorg. Chem. 1981, 20, 4033-4035
    • (1981) Inorg. Chem. , vol.20 , pp. 4033-4035
    • Huheey, J.E.1
  • 54
    • 12044258501 scopus 로고
    • Ab initio study of structures and stabilities of substituted lead compounds. Why is inorganic lead chemistry dominated by PbII but organolead chemistry by Pb(IV)?
    • Kaupp, M.; Schleyer, P. v. R. Ab initio study of structures and stabilities of substituted lead compounds. Why is inorganic lead chemistry dominated by PbII but organolead chemistry by Pb(IV)? J. Am. Chem. Soc. 1993, 115, 1061-1073
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1061-1073
    • Kaupp, M.1    Schleyer, V.P.R.2
  • 55
    • 0001349843 scopus 로고
    • Valence bond concepts applied to the molecular mechanics description of molecular shapes. 1. Application to nonhypervalent molecules of the P-block
    • Root, D. M.; Landis, C. R.; Cleveland, T. Valence bond concepts applied to the molecular mechanics description of molecular shapes. 1. Application to nonhypervalent molecules of the P-block J. Am. Chem. Soc. 1993, 115, 4201-4209
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4201-4209
    • Root, D.M.1    Landis, C.R.2    Cleveland, T.3
  • 56
    • 0000319606 scopus 로고    scopus 로고
    • Bent's rule and the structure of transition metal compounds
    • Jonas, V.; Boehme, C.; Frenking, G. Bent's rule and the structure of transition metal compounds Inorg. Chem. 1996, 35, 2097-2099
    • (1996) Inorg. Chem. , vol.35 , pp. 2097-2099
    • Jonas, V.1    Boehme, C.2    Frenking, G.3
  • 57
    • 0032762224 scopus 로고    scopus 로고
    • On the relation between π-Bonding, electronegativity, and bond angles in high-valent transition metal complexes
    • Kaupp, M. On the relation between π-Bonding, electronegativity, and bond angles in high-valent transition metal complexes Chem. - Eur. J. 1999, 5, 3631-3643
    • (1999) Chem. - Eur. J. , vol.5 , pp. 3631-3643
    • Kaupp, M.1
  • 58
    • 0000297714 scopus 로고    scopus 로고
    • 2Ru moiety: Preparation, substituent effects, and silylene character in the Ru-Si bond
    • 2Ru moiety: Preparation, substituent effects, and silylene character in the Ru-Si bond Organometallics 1999, 18, 1419-1429
    • (1999) Organometallics , vol.18 , pp. 1419-1429
    • Lemke, F.R.1    Galat, K.J.2    Youngs, W.J.3
  • 61
    • 34249297001 scopus 로고    scopus 로고
    • Substituted anilines: The tug-of-war between pyramidalization and resonance inside and outside of crystal cavities
    • Alabugin, I. V.; Manoharan, M.; Buck, M.; Clark, R. Substituted anilines: The tug-of-war between pyramidalization and resonance inside and outside of crystal cavities J. Mol. Struct. (THEOCHEM) 2007, 813, 21-27
    • (2007) J. Mol. Struct. (THEOCHEM) , vol.813 , pp. 21-27
    • Alabugin, I.V.1    Manoharan, M.2    Buck, M.3    Clark, R.4
  • 62
    • 0035840148 scopus 로고    scopus 로고
    • New Synthetic and structural aspects in the chemistry of alkylaluminum fluorides. The mutual influence of hard and soft ligands and the hybridization as rigorous structural criterion
    • Ferbinteanu, M.; Roesky, H. W.; Cimpoesu, F.; Atanasov, M.; Kopke, S.; Herbst-Irmer, R. New Synthetic and structural aspects in the chemistry of alkylaluminum fluorides. The mutual influence of hard and soft ligands and the hybridization as rigorous structural criterion Inorg. Chem. 2001, 40, 4947-4955
    • (2001) Inorg. Chem. , vol.40 , pp. 4947-4955
    • Ferbinteanu, M.1    Roesky, H.W.2    Cimpoesu, F.3    Atanasov, M.4    Kopke, S.5    Herbst-Irmer, R.6
  • 63
    • 84857551498 scopus 로고    scopus 로고
    • Relating bond angles of dihalo- and tetrahydro - Methanes, -silanes, and -germanes to electronegativities
    • Kirschenbaum, L. J.; Ruekberg, B. Relating bond angles of dihalo- and tetrahydro - methanes, -silanes, and -germanes to electronegativities J. Chem. Educ. 2012, 89, 351-354
    • (2012) J. Chem. Educ. , vol.89 , pp. 351-354
    • Kirschenbaum, L.J.1    Ruekberg, B.2
  • 64
    • 0242720554 scopus 로고    scopus 로고
    • Blue-shifted hydrogen bonds with proton-donors incapable of rehybridization
    • We deliberately did not include hypervalent compounds where hybridization is not well-defined and arguments based on this concept may be misleading
    • We deliberately did not include hypervalent compounds where hybridization is not well-defined and arguments based on this concept may be misleading: Wang, J.-T.; Feng, Y.; Liu, L.; Li, X.-S.; Guo, Q.-X. Blue-shifted hydrogen bonds with proton-donors incapable of rehybridization Chem. Lett. 2003, 32, 746-747
    • (2003) Chem. Lett. , vol.32 , pp. 746-747
    • Wang, J.-T.1    Feng, Y.2    Liu, L.3    Li, X.-S.4    Guo, Q.-X.5
  • 65
    • 2942585197 scopus 로고    scopus 로고
    • Blue-shifted and red-shifted hydrogen bonds in hypervalent rare-gas FRg-H···Y sandwiches
    • Alabugin, I. V.; Manoharan, M.; Weinhold, F. Blue-shifted and red-shifted hydrogen bonds in hypervalent rare-gas FRg-H···Y sandwiches J. Phys. Chem. A 2004, 108, 4720
    • (2004) J. Phys. Chem. A , vol.108 , pp. 4720
    • Alabugin, I.V.1    Manoharan, M.2    Weinhold, F.3
  • 66
    • 0038626673 scopus 로고    scopus 로고
    • revision E.01; Gaussian, Inc. Wallingford, CT.
    • Frisch, M. J.; Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 67
    • 70450206724 scopus 로고    scopus 로고
    • revision C.01; Gaussian, Inc. Wallingford, CT.
    • Frisch, M. J.; Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
    • (2009) Gaussian 09
    • Frisch, M.J.1
  • 68
    • 85005722995 scopus 로고
    • Natural bond orbital analysis of internal rotation barriers and related phenomena
    • For an illustrative rather than an exhaustive list of recent applications of the NBO method for analysis of chemical bonding see
    • For an illustrative rather than an exhaustive list of recent applications of the NBO method for analysis of chemical bonding see: Reed, A. E.; Weinhold, F. Natural bond orbital analysis of internal rotation barriers and related phenomena Isr. J. Chem. 1991, 31, 277-285
    • (1991) Isr. J. Chem. , vol.31 , pp. 277-285
    • Reed, A.E.1    Weinhold, F.2
  • 69
    • 0035978720 scopus 로고    scopus 로고
    • Hyperconjugation not steric repulsion leads to the staggered structure of ethane
    • Goodman, L.; Pophristic, V. T. Hyperconjugation not steric repulsion leads to the staggered structure of ethane Nature 2001, 411, 565
    • (2001) Nature , vol.411 , pp. 565
    • Goodman, L.1    Pophristic, V.T.2
  • 70
    • 0001412364 scopus 로고
    • Ab initio examination of anomeric effects in tetrahydropyrans, 1,3-dioxanes, and glucose
    • Salzner, U.; Schleyer, P. v. R. Ab initio examination of anomeric effects in tetrahydropyrans, 1,3-dioxanes, and glucose J. Org. Chem. 1994, 59, 2138-2155
    • (1994) J. Org. Chem. , vol.59 , pp. 2138-2155
    • Salzner, U.1    Schleyer, V.P.R.2
  • 71
    • 0029973440 scopus 로고    scopus 로고
    • Photoelectron spectra, ab initio scf mo, and natural bond orbital studies on stellenes. Long-range π/σ interactions
    • Gleiter, R.; Lange, H.; Borzyk, O. Photoelectron spectra, ab initio scf mo, and natural bond orbital studies on stellenes. Long-range π/σ interactions J. Am. Chem. Soc. 1996, 118, 4889-4895
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4889-4895
    • Gleiter, R.1    Lange, H.2    Borzyk, O.3
  • 75
    • 0035804966 scopus 로고    scopus 로고
    • Electronic delocalization contribution to the anomeric effect evaluated by computational methods
    • Cortes, F.; Tenorio, J.; Collera, O.; Cuevas, G. Electronic delocalization contribution to the anomeric effect evaluated by computational methods J. Org. Chem. 2001, 66, 2918-2924
    • (2001) J. Org. Chem. , vol.66 , pp. 2918-2924
    • Cortes, F.1    Tenorio, J.2    Collera, O.3    Cuevas, G.4
  • 76
    • 0035966171 scopus 로고    scopus 로고
    • Application of natural bond orbital analysis to delocalization and aromaticity in C-substituted tetrazoles
    • Sadlej-Sosnowska, N. Application of natural bond orbital analysis to delocalization and aromaticity in C-substituted tetrazoles J. Org. Chem. 2001, 66, 8737
    • (2001) J. Org. Chem. , vol.66 , pp. 8737
    • Sadlej-Sosnowska, N.1
  • 78
    • 0001382724 scopus 로고    scopus 로고
    • Ab initio computational studies of heterocycloalkynes: Structures, natural bond orders, ring strain energies, and isomerizations of cyclic iminoboranes and iminoalanes
    • Gilbert, T. M. Ab initio computational studies of heterocycloalkynes: Structures, natural bond orders, ring strain energies, and isomerizations of cyclic iminoboranes and iminoalanes Organometallics 2000, 19, 1160
    • (2000) Organometallics , vol.19 , pp. 1160
    • Gilbert, T.M.1
  • 79
    • 0035963771 scopus 로고    scopus 로고
    • 2+ cation with bases, base pairs, and nucleotides. Electron topology, natural bond orbital, electrostatic, and vibrational study
    • 2+ cation with bases, base pairs, and nucleotides. Electron topology, natural bond orbital, electrostatic, and vibrational study J. Phys. Chem. B 2001, 105, 6051
    • (2001) J. Phys. Chem. B , vol.105 , pp. 6051
    • Munoz, J.1    Sponer, J.2    Hobza, P.3    Orozco, M.4    Luque, F.J.5
  • 81
    • 0030859229 scopus 로고    scopus 로고
    • Through-bond orbital coupling, the parity rule, and the design of "superbridges" which exhibit greatly enhanced electronic coupling: A natural bond orbital analysis
    • Paddon-Row, M. N.; Shephard, M. J. Through-bond orbital coupling, the parity rule, and the design of "superbridges" which exhibit greatly enhanced electronic coupling: A natural bond orbital analysis J. Am. Chem. Soc. 1997, 119, 5355-5365
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5355-5365
    • Paddon-Row, M.N.1    Shephard, M.J.2
  • 83
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 1988, 88, 899-926
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 85
    • 36549103221 scopus 로고
    • Natural localized molecular orbitals
    • Reed, A. E.; Weinhold, F. Natural localized molecular orbitals J. Chem. Phys. 1985, 83, 1736-1740
    • (1985) J. Chem. Phys. , vol.83 , pp. 1736-1740
    • Reed, A.E.1    Weinhold, F.2
  • 87
    • 84878923966 scopus 로고    scopus 로고
    • Bent bonds and the antiperiplanar hypothesis as a simple model to predict diels-alder reactivity: Retrospective or perspective?
    • Deslongchamps, G.; Deslongchamps, P. Bent bonds and the antiperiplanar hypothesis as a simple model to predict diels-alder reactivity: Retrospective or perspective? Tetrahedron 2013, 69, 6022-6033
    • (2013) Tetrahedron , vol.69 , pp. 6022-6033
    • Deslongchamps, G.1    Deslongchamps, P.2


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