Interplay of Steric Hindrance and Hydrogen Bonding to Restrict Mono-O-substituted p-tert-Butylcalix[6] arenes in Cone Conformation

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1079-1085

  Oriol Magrans, J ^a,b   Rincón, Ana M ^a,b   Cuevas, Félix ^a,b   López Prados, Javier ^a,b   Nieto, Pedro M ^a,b   Pons, Miquel ^a,b   Prados, Pilar ^a,b   De Mendoza, Javier ^a,b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011190995     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971443x     Document Type: Article

References (51)

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30. Inversion is the result of flipping the four phenol rings in an "up" position to a "down" position and vice versa. This process exchanges the relative position of the calixarene benzylic protons with respect to the plane defined by the phenolic oxygens (see ref 10a). Pseudorotation was defined by us (see ref 10a) as the process that exchanges the phenolic rings that are projecting outside in a winged cone conformation, all atoms being thus virtually rotated over an angle of 120°. This process does not exchange the relative positions of the calixarene benzylic protons with respect to the plane defined by the phenolic oxygens. Pinched cone interconversion is a different pseudorotation process implying the exchange of four methylene groups between inside and outside positions. This process could be independent from inversion, but energy calculations suggest that a combined inversion - pseudorotation pathway has the lowest activation energy in vacuo (see ref 10b).
31. 10b
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49. For example, methylene proton a shows strong and medium ROESY signals with protons I and II; phenol B with I, II, and III; and phenol C and methylene proton c with III (Figure 1).
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