Synthetic Evolution of the Multifarene Cavity from Planar Predecessors

Chinna Ayya Swamy P, Ephrath Solel, Ofer Reany, Ehud Keinan

פרסום מחקרי: פרסום בכתב עתמאמרביקורת עמיתים

תקציר

The stepwise evolution of curved multifarene structures from planar precursors is demonstrated, highlighting three architectural design elements: 1) employment of various aromatic units, 2) changing the hybridization of the linking atoms from sp2 to sp3, and 3) rigidification of the system by the introduction of five-membered rings. Similar design elements have been employed to transform graphene sheets into curved carbon structures. Specifically, the stepwise synthetic evolution of multifarene[2+2], which has a curved, quite rigid structure, begins with a planar, tetraimine precursor, conversion to pairs of vicinal diamines, and the transformation of these pairs to cyclic thiourea groups. This process was probed by NMR spectroscopy and X-ray crystallography. Since varying the carbonylation conditions resulted in carbamates or thiocarbamates rather than the urea or thiourea isomers, the isomeric interconversion was studied both experimentally and by DFT computations. The carbamate versus urea preference was found to reflect either kinetic or thermodynamic control, respectively.

שפה מקוריתאנגלית
עמודים (מ-עד)15319-15328
מספר עמודים10
כתב עתChemistry - A European Journal
כרך24
מספר גיליון57
מזהי עצם דיגיטלי (DOIs)
סטטוס פרסוםפורסם - 12 אוק׳ 2018

הערה ביבליוגרפית

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

טביעת אצבע

להלן מוצגים תחומי המחקר של הפרסום 'Synthetic Evolution of the Multifarene Cavity from Planar Predecessors'. יחד הם יוצרים טביעת אצבע ייחודית.

פורמט ציטוט ביבליוגרפי