Pyramidalized olefins: A DFT study of bicyclo[2.1.1]-, -[3.2.1]-, and -[3.2.2]alkenes and their fused derivatives. Two rare examples of π-facially symmetric pyramidal olefins

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7134-7142

  Williams, Richard Vaughan ^a   Margetić, Davor ^b  

^a UNIVERSITY OF IDAHO   (United States)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

BENDING (DEFORMATION); CHEMICAL BONDS; DERIVATIVES; PROBABILITY DENSITY FUNCTION;

DENSITY FUNCTIONAL THEORY (DFT); NORBORNENES; OLEFINIC BONDS; PYRAMIDALIZATION;

OLEFINS;

ALKENE; ALKENE DERIVATIVE; BICYCLO COMPOUND; NORBORNENE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; STRUCTURE ANALYSIS;

EID: 5444267488     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0493626     Document Type: Article

References (22)

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21. 21 predicted a highly pyramidal ground state (ψ = 34.6°) for 28 using force field calculations. However, this level of theory is, in general, unreliable for the modelling of (potentially) pyramidal olefins as is demonstrated by Johnson's incorrect predictions that 2 and 11 are pyramidal (ψ = 27.3 and 7.5°, respectively).
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