Giovanni
Pierri, 
a
Rosaria
Schettini,
a
Francesco F.
Summa,
a
Francesco
De Riccardis,
a
Guglielmo
Monaco,
a
Irene
Izzo
*a
and
Consiglia
Tedesco
*a
a
Rosaria
Schettini,
a
Francesco F.
Summa,
a
Francesco
De Riccardis,
a
Guglielmo
Monaco,
a
Irene
Izzo
*a
and
Consiglia
Tedesco
*a
Abstract
Enantiomorphic right- and left-handed polyproline type I helices in four cyclic dodecapeptoids with methoxyethyl and propargyl side chains are observed for the first time by single crystal X-ray diffraction. The peculiar absence of NH⋯OC hydrogen bonds in peptoids unveils the role of intramolecular backbone-to-backbone CO⋯CO interactions and CH⋯OC hydrogen bonds in the stabilization of the macrocycle conformation. Moreover, intramolecular backbone-side chain C5 CH⋯OC hydrogen bonds emerge as a stabilizing factor.
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