Some difficulties encountered with AM1 and PM3 calculations

Tetrahedron

Volumn 54, Issue 42, 1998, Pages 12841-12852

  Nguyên Trong, Anh ^a   Frison, Gilles ^a   Solladié Cavallo, Arlette ^b   Metzner, Patrick ^c  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^b EHICS   (France)

^c UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; IMINE; ORGANIC COMPOUND; OXIME; PROPIONALDEHYDE; PROPYLENE;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; GAS; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032532591     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4020(98)00773-x     Document Type: Article

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47. ss orbital shortens the SS bond. This suggests that the lone pair repulsion is overestimated, which may explain why 13, a doubly excited state, lies only 26.3 kcal/mol above the ground state 11.
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57. 26 See also ref. 3h for similar results.
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64. 31 Cases where AM1 favours the endo isomer are also known: Pugnaud, S.; Masure, D.; Hallé, J-C.; Chaquin, P. J. Org. Chem. 1997, 62, 8687. The endo-exo difference is however much smaller than in ab initio calculations. Moreover, in the reactions studied, the endo isomer is also strongly favoured by coulombic attractions, which are somewhat exaggerated in AM1 and PM3 calculations.
65. 32 Gas phase reactions usually obey the Hammond postulate. See, inter alia: Tanaka, K.; Mackay, G. I.; Payzant, J. D.; Bohme, D. K. Can. J. Chem. 1976, 54, 1643. Shaik, S. S. Prog. Phys. Org. Chem. 1985, 15, 197. Evanseck, J. D.; Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1987, 109, 2349.
66. 32 Gas phase reactions usually obey the Hammond postulate. See, inter alia: Tanaka, K.; Mackay, G. I.; Payzant, J. D.; Bohme, D. K. Can. J. Chem. 1976, 54, 1643. Shaik, S. S. Prog. Phys. Org. Chem. 1985, 15, 197. Evanseck, J. D.; Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1987, 109, 2349.
67. 32 Gas phase reactions usually obey the Hammond postulate. See, inter alia: Tanaka, K.; Mackay, G. I.; Payzant, J. D.; Bohme, D. K. Can. J. Chem. 1976, 54, 1643. Shaik, S. S. Prog. Phys. Org. Chem. 1985, 15, 197. Evanseck, J. D.; Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1987, 109, 2349.
68. 33 PM3 gives analogous results.
69. 34 Hydrogen bonding may occur with an aldehydic hydrogen if the carbonyl group is activated by a Lewis acid: Corey, E. J.; Barnes-Seeman, D.; Lee. T. W. Tetrahedron Letters 1997, 38, 1699.
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