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Thermodynamic Template Effect in DCC
Josè Augusto Berrocal, Roberta Cacciapaglia, Stefano Di Stefano,
and Luigi Mandolini.
IMC-CNR Sezione Meccanismi di Reazione and Dipartimento di Chimica,
Università “Sapienza”di Roma, piazzale Aldo Moro 5, 00185, Roma
joseaugusto.berrocal@uniroma1.it
Dynamic Combinatorial Chemistry (DCC) studies the generation of libraries of
compounds which are fully interchangeable under mild conditions. 1 The most appealing
feature of DCC is the chance to amplify the yield of one of the above compounds by
means of the addition of an appropriate template (an ion or a neutral molecule) which
selectively binds and offers stabilization to that specific compound.
The acid-catalyzed transacetalation of formaldehyde acetals is a suitable reaction for the
generation of well-behaved Dynamic Libraries of cyclophane formals. In the present
communication we report the experimental results related to a quantitative definition of
thermodynamic template effect 2 and the results obtained with a new well-behaved
dynamic library of cyclophanes based on the bis[4-(hydroxymethyl)phenyl]methane
unit (Fig 1). 3
Fig 1. Dynamic library based on the bis[4-(hydroxymethyl)phenyl]methane unit.
References
1
Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.;
Otto, S., Chem. Rev., 2006, 106, 3652�3711;
2
Berrocal, J. A.; Cacciapaglia, R.; Di Stefano, S.; Mandolini, L., manuscript in
preparation.
3
Berrocal, J. A.; Cacciapaglia, R.; Di Stefano, S.; Mandolini, L., manuscript in
preparation.