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Optically active derivatives of terephthalic acid: four crystal structures from two powder patterns
Author(s) -
Veselovsky Vladimir V.,
Lozanova Antonina V.,
Isaeva Vera I.,
Lobova Anna A.,
Fitch Andrew N.,
Chernyshev Vladimir V.
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618001705
Subject(s) - terephthalic acid , optically active , materials science , crystal (programming language) , chemistry , organic chemistry , composite material , polyester , computer science , programming language
A novel important class of nanoporous crystalline solids, metal–organic frameworks (MOFs), composed of organic ligands (linkers) and metal ions, is now considered as a platform for the development of various functional hybrid materials. In order to design new MOF‐based asymmetric catalysts, two terephthalic acid derivatives, namely 2‐{[1‐(1‐ tert ‐butoxycarbonyl)‐ l ‐prolyl]amino}terephthalic acid, C 18 H 22 N 2 O 7 , (1), and 2‐( l ‐prolylamino)terephthalic acid, C 13 H 14 N 2 O 5 , (2), which could find potential applications as chiral linkers for the construction of enantioselective MOFs, were synthesized and their powder samples were measured at synchrotron station ID22 (ESRF). Each sample contained two unknown crystalline phases, so four new crystal structures were determined, namely, the 2.24‐hydrate of (1), (1 a ) (space group C 222 1 ), and the 2.08‐hydrate of (1), (1 b ) ( P 222 1 ), which are crystallohydrates, and two polymorphs of (2), i.e. (2 a ) ( C 222 1 ) and (2 b ) ( P 2 1 2 1 2 1 ), and were validated with DFT‐d (dispersion‐corrected density functional theory) optimizations.