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Weak Hydrogen Bonding in the Structures of Three Double-Acylated Aminoantipyrines

Lookup NU author(s): Dr Michael HallORCiD, Dr Paul Waddell

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Abstract

The structures of three doubly-acylated 4-aminoantipyrine (AP) compounds where the aryl substituent is varied are reported and analysed in terms of their relative conformation, intermolecular interactions and overall packing. The compounds were crystallised using the Encapsulated Nanodroplet Crystallisation (ENaCt) protocol. Where previous, singly-acylated AP compounds produced structures with obvious, classical hydrogen bonding motifs, the doubly-acylated derivatives lack classical donors and therefore exhibit weak C-H hydrogen bonds and interactions involving the π-system. All three form bifurcated C-H‧‧‧O interactions with either dimer or chain motifs with the other structure-directing interactions being dependant on the nature of the aryl substituent.

Publication metadata

Author(s): Mardiana L, Al Abdali AB, Hall MJ, Al Mamari HH, Waddell PG

Publication type: Article

Publication status: Published

Journal: Acta Crystallographica Section C: Structural Chemistry

Year: 2025

Volume: C81

Issue: 12

Print publication date: 01/12/2025

Online publication date: 10/11/2025

Acceptance date: 30/10/2025

Date deposited: 12/11/2025

ISSN (electronic): 2053-2296

Publisher: International Union of Crystallography Wiley

URL: https://doi.org/10.1107/S2053229625009581

DOI: 10.1107/S2053229625009581

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