Two closely related {4‐[(N‐substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids. Issue 1 (14th December 2016)

• Record Type: Journal Article
• Authors: Zhang, Rui; Zhang, Yundi; Ge, Chunhua; Miao, Jinpeng; Zhang, Xiangdong
• Is Part Of: Acta crystallographica. Volume 73:Issue 1(2017)
• Page Start: 57
• Page End: 60
• Publication Date: 2016-12-14
• Subjects: phosphonic acid diethyl esters -- crystal structure -- C—P bonds -- boronic acids; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229616019707
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : Two new B, P, N‐containing compounds were synthesized via simple reactions and were structurally characterized. Intermolecular hydrogen bonds link the independent molecules into supramolecular networks. Abstract : Organic phosphonic acids and organic phosphonic acid esters have been of much interest due to their applications in the fields of medicine, agriculture and industrial chemistry. Boronic acids can act as synthetic intermediates and building blocks and are used in sensing, protein manipulation, therapeutics, biological labelling and separation. The additional introduction of an aminophosphonic acid group into a boronic acid may give new opportunities for application. To study the structure of such multifunctional compounds, we prepared two new derivatives which can be easily converted to the corresponding phosphonic acids. In the title compounds, {4‐[(butylamino)(diethoxyphosphoryl)methyl]phenyl}boronic acid monohydrate, C15 H27 BNO5 P·H2 O, (I), and {4‐[(diethoxyphosphoryl)(4‐nitroanilino)methyl]phenyl}boronic acid, C17 H22 BN2 O7 P, (II), three different substituents are attached to a central C—H group, namely 4‐boronophenyl, diethoxyphosphoryl and amine. Compound (I) crystallizes as a monohydrate and OB —H…N hydrogen bonds link neighbouring molecules into chains along the [001] direction. The solvent water molecule connects two such chains running in opposite directions. Compound (II) crystallizes as an ansolvate and classical hydrogen bonds result in a layer structure in the (001) plane.