- Substituent Effects in Parallel-Displaced π–π Stacking Interactions: Distance Matters
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Host–guest systems with Rebek imide type receptors and a 2,6-di(isobutyramido)pyridine ligand were employed to investigate substituent effects in parallel-displaced π–π stacking interactions. Changing the intermolecular distance between the para substitue
- Riwar, Leslie-Joana,Trapp, Nils,Kuhn, Bernd,Diederich, Fran?ois
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supporting information
p. 11252 - 11257
(2017/09/02)
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- Rapid cleavage of cyclic tertiary amides of Kemp's triacid: Effects of ring structure
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The piperidyl and prolyl amides of Kemp's triacid (7 and 8, respectively) have been prepared and their rates of intramolecular acylolysis measured as a function of pD. The piperidyl derivative 7 reacts approximately four-times faster (e.g., t1/2=3min at 20°C and pD7.7) than the previously reported pyrrolidyl and methylphenethyl amide derivatives, while the prolyl derivative 8 reacts two-times more slowly (e.g., t1/2=30min at 20°C and pD7.8). Molecular-mechanics calculations indicate that the nonbonded interactions in the piperidyl derivative 7 are distinct from those in the prolyl, pyrrolidyl, and methylphenethyl amide derivatives, a result that supports the suggestion that ground-state pseudoallylic strain contributes to the enormous reactivity of Kemp's triacid tertiary amides. In sum, the results reported indicate that the Kemp's triacid scaffolding provides a general means of activating tertiary amide derivatives.
- Dougan, Michael L.,Chin, Jonathan L.,Solt, Ken,Hansen, David E.
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p. 4153 - 4156
(2007/10/03)
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- 3,5,7-Trimethyl-1-azatricyclo[3.3.1.13,7]decan-2-ylidene, an Aminocarbene without π conjugation
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3,5,7-Trimethyl-1-azatricyclo[3.3.1.13,7]decan-2-ylidene, an aminocarbene without π conjugation, has been generated from the corresponding tosylhydrazone salt. Addition of the carbene to alkenes is stereospecifically cis, thus showing that the
- Ye, Qing,Komarov, Igor V.,Kirby, Anthony J.,Jones Jr., Maitland
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p. 9288 - 9294
(2007/10/03)
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- Molecular recognition with convergent functional groups. 6. Synthetic and structural studies with a model receptor for nucleic acid components
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Experimental details are given for the synthesis and characterization of a new class of model receptors for adenine derivatives. The molecules feature an imide function and a suitably placed aromatic surface that permits simultaneous base pairing and aryl
- Askew,Ballester,Buhr,Jeong,Jones,Parris,Williams,Rebek Jr.
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p. 1082 - 1090
(2007/10/02)
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- Synthesis and Conformational Analysis of cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic Acid
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Conversion of 3,5,7-trimethyladamantan-1-ol to a hypobromite, fragmentation in situ, and oxidation with KMnO4 generate the lactone, 6, of cis,cis-1,3,5-trimethyl-1-(hydroxymethyl)cyclohexane-3,5-dicarboxylic acid, which can in turn be oxidized by RuO4-HIO
- Kemp, D. S.,Petrakis, Konstantinos S.
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p. 5140 - 5143
(2007/10/02)
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