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Volumn 1, Issue 2, 2011, Pages 164-171

Rotational barriers in alkanes

Author keywords

[No Author keywords available]

Indexed keywords

HYPERCONJUGATION EFFECTS; HYPERCONJUGATIVE INTERACTIONS; LOCALIZED ORBITALS; NATURAL BOND ORBITAL ANALYSIS; QUANTUM MECHANICAL; ROTATIONAL BARRIERS; STAGGERED STRUCTURES; VALENCE BOND THEORY;

EID: 84859572671     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.22     Document Type: Article
Times cited : (42)

References (58)
  • 1
    • 34250344516 scopus 로고
    • Hindered rotation of the methyl groups in ethane
    • Kemp JD, Pitzer KS. Hindered rotation of the methyl groups in ethane. J Chem Phys 1936, 4:749.
    • (1936) J Chem Phys , vol.4 , pp. 749
    • Kemp, J.D.1    Pitzer, K.S.2
  • 2
    • 0001088348 scopus 로고
    • Thermodynamic functions for molecules having restricted internal rotations
    • Pitzer KS. Thermodynamic functions for molecules having restricted internal rotations. J Chem Phys 1937, 5:469-472.
    • (1937) J Chem Phys , vol.5 , pp. 469-472
    • Pitzer, K.S.1
  • 3
    • 0037020383 scopus 로고    scopus 로고
    • Teaching the right reasons: Lessons from the mistaken origin of the rotational barrier in ethane
    • Schreiner PR. Teaching the right reasons: Lessons from the mistaken origin of the rotational barrier in ethane. Angew Chem Int Ed 2002, 41:3579-3581.
    • (2002) Angew Chem Int Ed , vol.41 , pp. 3579-3581
    • Schreiner, P.R.1
  • 5
    • 33748885435 scopus 로고    scopus 로고
    • Carbon-carbon rotational barriers in butane, 1-butene, and 1,3-butadiene
    • Murcko MA, Castejon H, Wiberg KB. Carbon-carbon rotational barriers in butane, 1-butene, and 1, 3-butadiene. J Phys Chem 1996, 100:16162-16168.
    • (1996) J Phys Chem , vol.100 , pp. 16162-16168
    • Murcko, M.A.1    Castejon, H.2    Wiberg, K.B.3
  • 6
    • 33749368925 scopus 로고    scopus 로고
    • Ultrafast carbon-carbon single-bond rotational isomerization in room-temperature solution
    • Zheng J, Kwak K, Xie J, Fayer MD. Ultrafast carbon-carbon single-bond rotational isomerization in room-temperature solution. Science 2006, 313:1951-1955.
    • (2006) Science , vol.313 , pp. 1951-1955
    • Zheng, J.1    Kwak, K.2    Xie, J.3    Fayer, M.D.4
  • 7
    • 70350705875 scopus 로고    scopus 로고
    • A theoretical view on the conformer stabilization of butane
    • Cormanich RA, Freitas MP. A theoretical view on the conformer stabilization of butane. J Org Chem 2009, 74:8384-8387.
    • (2009) J Org Chem , vol.74 , pp. 8384-8387
    • Cormanich, R.A.1    Freitas, M.P.2
  • 8
    • 33750447020 scopus 로고    scopus 로고
    • Effect of solvation and confinement on the trans-gauche isomerization reaction in n-butane
    • Travis KP, Searles DJ. Effect of solvation and confinement on the trans-gauche isomerization reaction in n-butane. J Chem Phys 2006, 125:164501.
    • (2006) J Chem Phys , vol.125 , pp. 164501
    • Travis, K.P.1    Searles, D.J.2
  • 9
    • 58149147156 scopus 로고    scopus 로고
    • Role of short-range electrostatics in torsional potentials
    • Darley MG, Popelier PLA. Role of short-range electrostatics in torsional potentials. J Phys Chem A 2008, 112:12954-12965.
    • (2008) J Phys Chem A , vol.112 , pp. 12954-12965
    • Darley, M.G.1    Popelier, P.L.A.2
  • 10
    • 8644224198 scopus 로고    scopus 로고
    • Secondary-structure preferences of force fields for proteins evaluated by generalized-ensemble simulations
    • Yoda T, Sugita Y, Okamoto Y. Secondary-structure preferences of force fields for proteins evaluated by generalized-ensemble simulations. Chem Phys 2004, 307:269-283.
    • (2004) Chem Phys , vol.307 , pp. 269-283
    • Yoda, T.1    Sugita, Y.2    Okamoto, Y.3
  • 11
    • 85047692291 scopus 로고    scopus 로고
    • Empirical force-field assessment: The interplay between backbone torsions and noncovalent term scaling
    • Sorin EJ, Pande VS. Empirical force-field assessment: The interplay between backbone torsions and noncovalent term scaling. J Comput Chem 2005, 26:682-690.
    • (2005) J Comput Chem , vol.26 , pp. 682-690
    • Sorin, E.J.1    Pande, V.S.2
  • 12
    • 63749094067 scopus 로고    scopus 로고
    • Effect of torsional potential on the predicted phase behavior of n-alkanes
    • Bernard-Brunela DA, Potoff JJ. Effect of torsional potential on the predicted phase behavior of n-alkanes. Fluid Phase Equilib 2009, 279:100-104.
    • (2009) Fluid Phase Equilib , vol.279 , pp. 100-104
    • Bernard-Brunela, D.A.1    Potoff, J.J.2
  • 13
    • 0002958089 scopus 로고
    • Barriers to rotation and inversion
    • Schaefer III HF, ed. Vol. New York and London: Plenum Press;
    • Payne PW, Allen LC. Barriers to rotation and inversion. In: Schaefer III HF, ed. Mordern Theoretical Chemistry. Vol. 4. New York and London: Plenum Press; 1977, 29-108.
    • (1977) Mordern Theoretical Chemistry , vol.4 , pp. 29-108
    • Payne, P.W.1    Allen, L.C.2
  • 14
    • 33947364342 scopus 로고    scopus 로고
    • Rotational barriers: Ab initio computations
    • Schelyer PvR, ed. Berlin: John Wiley & Sons;
    • Wiberg KB. Rotational barriers: Ab initio computations. In: Schelyer PvR, ed. Encyclopedia of Computational Chemistry. Berlin: John Wiley & Sons; 1998, 2518-2525.
    • (1998) Encyclopedia of Computational Chemistry , pp. 2518-2525
    • Wiberg, K.B.1
  • 15
    • 0000918305 scopus 로고
    • The Infra-Red spectrum of C2H6
    • Smith LG. The Infra-Red spectrum of C2H6. J Chem Phys 1949, 17:139.
    • (1949) J Chem Phys , vol.17 , pp. 139
    • Smith, L.G.1
  • 16
    • 3943111261 scopus 로고
    • Potential energies for rotation about single bonds
    • Pitzer KS. Potential energies for rotation about single bonds. Discuss Faraday Soc 1951, 10:66-73.
    • (1951) Discuss Faraday Soc , vol.10 , pp. 66-73
    • Pitzer, K.S.1
  • 17
    • 0001516989 scopus 로고
    • The problem of barriers to international rotation in molecules
    • Wilson Jr EB. The problem of barriers to international rotation in molecules. Adv Chem Phys 1959, 2:367.
    • (1959) Adv Chem Phys , vol.2 , pp. 367
    • Wilson Jr, E.B.1
  • 18
    • 0000711866 scopus 로고
    • Quantum-mechanical studies on the origin of barriers to internal rotation about single bonds
    • Pitzer RM. Quantum-mechanical studies on the origin of barriers to internal rotation about single bonds. Acc Chem Res 1983, 16:207-210.
    • (1983) Acc Chem Res , vol.16 , pp. 207-210
    • Pitzer, R.M.1
  • 19
    • 0346150002 scopus 로고    scopus 로고
    • The barrier to internal rotation in ethane
    • Halpern AM, Glendening ED. The barrier to internal rotation in ethane. J Chem Phys 2003, 119:11186-11191.
    • (2003) J Chem Phys , vol.119 , pp. 11186-11191
    • Halpern, A.M.1    Glendening, E.D.2
  • 20
    • 4344674643 scopus 로고    scopus 로고
    • Origin of rotation and inversion barriers
    • Bohn RK. Origin of rotation and inversion barriers. J Phys Chem A 2004, 108:6814-6816.
    • (2004) J Phys Chem A , vol.108 , pp. 6814-6816
    • Bohn, R.K.1
  • 21
    • 0000790487 scopus 로고
    • An intrinsic reaction coordinate calculation of the torsional potential in ethane: Comparison of the computationally and experimentally derived torsional transitions and the rotational barrier
    • Allen LC. An intrinsic reaction coordinate calculation of the torsional potential in ethane: Comparison of the computationally and experimentally derived torsional transitions and the rotational barrier. Chem Phys Lett 1968, 2:597-601.
    • (1968) Chem Phys Lett , vol.2 , pp. 597-601
    • Allen, L.C.1
  • 23
    • 0001578369 scopus 로고
    • A butane analogue, 3-hexyne, is eclipsed
    • Lowe JP. A butane analogue, 3-hexyne, is eclipsed. Science 1973, 179:527-532.
    • (1973) Science , vol.179 , pp. 527-532
    • Lowe, J.P.1
  • 24
    • 33845560514 scopus 로고
    • Bond-function analysis of rotational barriers: ethane
    • Brunck TK, Weinhold F. Bond-function analysis of rotational barriers: ethane. J Am Chem Soc 1979, 101:1700-1709.
    • (1979) J Am Chem Soc , vol.101 , pp. 1700-1709
    • Brunck, T.K.1    Weinhold, F.2
  • 26
    • 0001767684 scopus 로고
    • Barrier to internal rotation in ethane from the microwave spectrum of CH3CHD2
    • Hirota E, Saito S, Endo Y. Barrier to internal rotation in ethane from the microwave spectrum of CH3CHD2. J Chem Phys 1979, 71:1183-1187.
    • (1979) J Chem Phys , vol.71 , pp. 1183-1187
    • Hirota, E.1    Saito, S.2    Endo, Y.3
  • 28
    • 34547269077 scopus 로고    scopus 로고
    • Steric effect: a quantitative description from density functional theory
    • Liu S. Steric effect: a quantitative description from density functional theory. J Chem Phys 2007, 126:244103.
    • (2007) J Chem Phys , vol.126 , pp. 244103
    • Liu, S.1
  • 29
    • 0000717334 scopus 로고
    • Intensities of electronic transitions in molecular spectra. IV. Cyclic dienes and hyperconjugation
    • Mulliken RS. Intensities of electronic transitions in molecular spectra. IV. Cyclic dienes and hyperconjugation. J Chem Phys 1939, 7:339-352.
    • (1939) J Chem Phys , vol.7 , pp. 339-352
    • Mulliken, R.S.1
  • 30
    • 33947290344 scopus 로고
    • Localized charge distributions. I. General theory, energy partitioning, and the internal rotation barrier in ethane
    • England W, Gordon MS. Localized charge distributions. I. General theory, energy partitioning, and the internal rotation barrier in ethane. J Am Chem Soc 1971, 93:4649-4657.
    • (1971) J Am Chem Soc , vol.93 , pp. 4649-4657
    • England, W.1    Gordon, M.S.2
  • 32
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed AE, Curtiss LA, 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
  • 33
    • 85005722995 scopus 로고
    • Natural bond orbital analysis of internal rotation barriers and related phenomena
    • Reed AE, 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
  • 34
    • 84918635840 scopus 로고
    • Electronic structures and reactivities of pyramidal alkenes and carbonyls
    • Houk KN, Rondan NG, Brown FK. Electronic structures and reactivities of pyramidal alkenes and carbonyls. Isr J Chem 1983, 23:3-9.
    • (1983) Isr J Chem , vol.23 , pp. 3-9
    • Houk, K.N.1    Rondan, N.G.2    Brown, F.K.3
  • 35
    • 0020821964 scopus 로고
    • Electronic origins and consequences of pyramidalization of asymmetric alkenes in ground and triplet excited states
    • Houk KN, Rondan NG, Brown FK, Jorgensen WL, Madura JD, Spellmeyer DC. Electronic origins and consequences of pyramidalization of asymmetric alkenes in ground and triplet excited states. J Am Chem Soc 1983, 105:5980-5988.
    • (1983) J Am Chem Soc , vol.105 , pp. 5980-5988
    • Houk, K.N.1    Rondan, N.G.2    Brown, F.K.3    Jorgensen, W.L.4    Madura, J.D.5    Spellmeyer, D.C.6
  • 37
    • 0002960487 scopus 로고    scopus 로고
    • Flexing analysis of steric exchange repulsion accompanying ethane internal rotation
    • Goodman L, Gu H. Flexing analysis of steric exchange repulsion accompanying ethane internal rotation. J Chem Phys 1998, 109:72-78.
    • (1998) J Chem Phys , vol.109 , pp. 72-78
    • Goodman, L.1    Gu, H.2
  • 38
    • 0001220485 scopus 로고    scopus 로고
    • Flexing analysis of ethane internal rotation energetics
    • Goodman L, Gu H, Pophristic V. Flexing analysis of ethane internal rotation energetics. J Chem Phys 1999, 110:4268-4275.
    • (1999) J Chem Phys , vol.110 , pp. 4268-4275
    • Goodman, L.1    Gu, H.2    Pophristic, V.3
  • 39
    • 0033371601 scopus 로고    scopus 로고
    • Origin of methyl internal rotation barriers
    • Goodman L, Pophristic V, Weinhold F. Origin of methyl internal rotation barriers. Acc Chem Res 1999, 32:983-993.
    • (1999) Acc Chem Res , vol.32 , pp. 983-993
    • Goodman, L.1    Pophristic, V.2    Weinhold, F.3
  • 40
    • 0035978720 scopus 로고    scopus 로고
    • Hyperconjugation not steric repulsion leads to the staggered structure of ethane
    • Pophristic V, Goodman L. Hyperconjugation not steric repulsion leads to the staggered structure of ethane. Nature 2001, 411:565-568.
    • (2001) Nature , vol.411 , pp. 565-568
    • Pophristic, V.1    Goodman, L.2
  • 41
    • 0039164835 scopus 로고
    • Antisymmetrization effects in bond-orbital models of internal rotation barriers
    • Corcoran CT, Weinhold F. Antisymmetrization effects in bond-orbital models of internal rotation barriers. J Chem Phys 1980, 72:2866-2868.
    • (1980) J Chem Phys , vol.72 , pp. 2866-2868
    • Corcoran, C.T.1    Weinhold, F.2
  • 42
    • 0141522603 scopus 로고    scopus 로고
    • Rebuttal to the Bickelhaupt--Baerends case for steric repulsion causing the staggeredconformation of ethane
    • Weinhold F, Rebuttal to the Bickelhaupt--Baerends case for steric repulsion causing the staggeredconformation of ethane. Angew Chem Int Ed 2003, 42:4188-4194.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 4188-4194
    • Weinhold, F.1
  • 43
    • 0141745664 scopus 로고    scopus 로고
    • The case for steric repulsion causing the staggered conformation of ethane
    • Bickelhaupt FM, Baerends EJ. The case for steric repulsion causing the staggered conformation of ethane. Angew Chem Int Ed 2003, 42:4183-4188.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 4183-4188
    • Bickelhaupt, F.M.1    Baerends, E.J.2
  • 44
    • 3042782943 scopus 로고    scopus 로고
    • The magnitude of hyperconjugation in ethane: A perspective from ab initio valence bond theory
    • Mo Y, Wu W, Song L, Lin M, Zhang Q, Gao J. The magnitude of hyperconjugation in ethane: A perspective from ab initio valence bond theory. Angew Chem Int Ed 2004, 43:1986-1990.
    • (2004) Angew Chem Int Ed , vol.43 , pp. 1986-1990
    • Mo, Y.1    Wu, W.2    Song, L.3    Lin, M.4    Zhang, Q.5    Gao, J.6
  • 45
    • 15944403519 scopus 로고    scopus 로고
    • Steric strain versus hyperconjugative stabilization in ethane congeners
    • Song L, Lin Y, Wu W, Zhang Q, Mo Y. Steric strain versus hyperconjugative stabilization in ethane congeners. J Phys Chem A 2005, 109:2310-2316.
    • (2005) J Phys Chem A , vol.109 , pp. 2310-2316
    • Song, L.1    Lin, Y.2    Wu, W.3    Zhang, Q.4    Mo, Y.5
  • 46
    • 0000966560 scopus 로고    scopus 로고
    • Theoretical analysis of electronic delocalization
    • Mo Y, Peyerimhoff SD. Theoretical analysis of electronic delocalization. J Chem Phys 1998, 109:1687-1697.
    • (1998) J Chem Phys , vol.109 , pp. 1687-1697
    • Mo, Y.1    Peyerimhoff, S.D.2
  • 47
    • 0000110457 scopus 로고    scopus 로고
    • Energy decomposition analysis of intermolecular interactions using a block-localized wave function approach
    • Mo Y, Gao J, Peyerimhoff SD. Energy decomposition analysis of intermolecular interactions using a block-localized wave function approach. J Chem Phys 2000, 112:5530-5538.
    • (2000) J Chem Phys , vol.112 , pp. 5530-5538
    • Mo, Y.1    Gao, J.2    Peyerimhoff, S.D.3
  • 49
    • 33644516915 scopus 로고    scopus 로고
    • An energetic measure of aromaticity and antiaromaticity based on the Pauling-Wheland resonance energies
    • Mo Y, Schleyer PvR. An energetic measure of aromaticity and antiaromaticity based on the Pauling-Wheland resonance energies. Chem Eur J 2006, 12:2009-2020.
    • (2006) Chem Eur J , vol.12 , pp. 2009-2020
    • Mo, Y.1    Schleyer, P.2
  • 50
    • 34548598669 scopus 로고    scopus 로고
    • The block-localized wavefunction (BLW) method at the density functional theory (DFT) level
    • Mo Y, Song L, Lin Y. The block-localized wavefunction (BLW) method at the density functional theory (DFT) level. J Phys Chem A 2007, 111:8291-8301.
    • (2007) J Phys Chem A , vol.111 , pp. 8291-8301
    • Mo, Y.1    Song, L.2    Lin, Y.3
  • 51
    • 33947379737 scopus 로고    scopus 로고
    • Theoretical analysis of the rotational barrier of ethane
    • Mo Y, Gao J. Theoretical analysis of the rotational barrier of ethane. Acc Chem Res 2007, 40:113-119.
    • (2007) Acc Chem Res , vol.40 , pp. 113-119
    • Mo, Y.1    Gao, J.2
  • 52
    • 0010299174 scopus 로고
    • Enthalpy difference between conformers of n-butane and the potential function governing conformational interchange
    • Herrebout WA, Van Der Veken BJ, Wang A, Durig JR. Enthalpy difference between conformers of n-butane and the potential function governing conformational interchange. J Phys Chem 1995, 99:578-585.
    • (1995) J Phys Chem , vol.99 , pp. 578-585
    • Herrebout, W.A.1    Van Der Veken, B.J.2    Wang, A.3    Durig, J.R.4
  • 53
    • 34548262693 scopus 로고    scopus 로고
    • Is there a general rule for the gauche effect in the conformational isomerism of 1,2-disubstituted ethanes
    • Freitas MP, Rittner R. Is there a general rule for the gauche effect in the conformational isomerism of 1, 2-disubstituted ethanes? J Phys Chem A 2007, 111:7233-7236.
    • (2007) J Phys Chem A , vol.111 , pp. 7233-7236
    • Freitas, M.P.1    Rittner, R.2
  • 54
    • 49149123907 scopus 로고    scopus 로고
    • Toward understanding the nature of internal rotation barriers with a new energy partition scheme: Ethane and n-butane
    • Liu S, Govind N. Toward understanding the nature of internal rotation barriers with a new energy partition scheme: Ethane and n-butane. J Phys Chem A 2008, 112:6690-6699.
    • (2008) J Phys Chem A , vol.112 , pp. 6690-6699
    • Liu, S.1    Govind, N.2
  • 55
    • 77950982838 scopus 로고    scopus 로고
    • A critical analysis on the rotation barriers in butane
    • Mo Y. A critical analysis on the rotation barriers in butane. J Org Chem 2010, 75:2733-2736.
    • (2010) J Org Chem , vol.75 , pp. 2733-2736
    • Mo, Y.1
  • 56
    • 69249112257 scopus 로고    scopus 로고
    • Conformational dependence of s-electron delocalization in linear chains: Permethylated oligosilanes
    • Bande A, Michl J. Conformational dependence of s-electron delocalization in linear chains: Permethylated oligosilanes. Chem Eur J 2009, 15:8504-8517.
    • (2009) Chem Eur J , vol.15 , pp. 8504-8517
    • Bande, A.1    Michl, J.2


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