Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation

Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation

The solid-state behaviour of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to Pt<sup>II</sup>, have been extensively studied using single crystal X-ray crystallography. In the first library, isomeric diphosphines of the type Ph<sub>...

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Autores principales: Peter De’Ath, Mark R. J. Elsegood, Noelia M. Sanchez-Ballester, Martin B. Smith
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Lenguaje:EN
Publicado: MDPI AG 2021
Materias:
amide groups
isomers
late-transition metals
P-ligands
phenols
secondary interactions
Organic chemistry
QD241-441
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spelling oai:doaj.org-article:121a97a7c71d47f38ce993cbb44ea0372021-11-25T18:27:25ZLow-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation10.3390/molecules262268091420-3049https://doaj.org/article/121a97a7c71d47f38ce993cbb44ea0372021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6809https://doaj.org/toc/1420-3049The solid-state behaviour of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to Pt<sup>II</sup>, have been extensively studied using single crystal X-ray crystallography. In the first library, isomeric diphosphines of the type Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub> [<b>1a</b>–<b>e</b>; Ar = C<sub>6</sub>H<sub>3</sub>(Me)(OH)] and, in the second library, amide-functionalised, isomeric ligands Ph<sub>2</sub>PCH<sub>2</sub>N{CH<sub>2</sub>C(O)NH(Ar)}CH<sub>2</sub>PPh<sub>2</sub> [<b>2a</b>–<b>e</b>; Ar = C<sub>6</sub>H<sub>3</sub>(Me)(OH)], were synthesised by reaction of Ph<sub>2</sub>PCH<sub>2</sub>OH and the appropriate amine in CH<sub>3</sub>OH, and isolated as colourless solids or oils in good yield. The non-methyl, substituted diphosphines Ph<sub>2</sub>PCH<sub>2</sub>N{CH<sub>2</sub>C(O)NH(Ar)}CH<sub>2</sub>PPh<sub>2</sub> [<b>2f</b>, Ar = 3-C<sub>6</sub>H<sub>4</sub>(OH); <b>2g</b>, Ar = 4-C<sub>6</sub>H<sub>4</sub>(OH)] and Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub> [<b>3</b>, Ar = 3-C<sub>6</sub>H<sub>4</sub>(OH)] were also prepared for comparative purposes. Reactions of <b>1a</b>–<b>e</b>, <b>2a</b>–<b>g</b>, or <b>3</b> with PtCl<sub>2</sub>(η<sup>4</sup>-cod) afforded the corresponding square-planar complexes <b>4a</b>–<b>e</b>, <b>5a</b>–<b>g</b>, and <b>6</b> in good to high isolated yields. All new compounds were characterised using a range of spectroscopic (<sup>1</sup>H, <sup>31</sup>P{<sup>1</sup>H}, FT–IR) and analytical techniques. Single crystal X-ray structures have been determined for <b>1a</b>, <b>1b</b>∙CH<sub>3</sub>OH, <b>2f</b>∙CH<sub>3</sub>OH, <b>2g</b>, <b>3</b>, <b>4b</b>∙(CH<sub>3</sub>)<sub>2</sub>SO, <b>4c</b>∙CHCl<sub>3</sub>, <b>4d</b>∙½Et<sub>2</sub>O, <b>4e</b>∙½CHCl<sub>3</sub>∙½CH<sub>3</sub>OH, <b>5a</b>∙½Et<sub>2</sub>O, <b>5b</b>, <b>5c</b>∙¼H<sub>2</sub>O, <b>5d</b>∙Et<sub>2</sub>O, and <b>6</b>∙(CH<sub>3</sub>)<sub>2</sub>SO. The free phenolic group in <b>1b</b>∙CH<sub>3</sub>OH, <b>2f</b>∙CH<sub>3</sub>OH<sub>,</sub><b>2g</b>, <b>4b</b>∙(CH<sub>3</sub>)<sub>2</sub>SO, <b>5a</b>∙½Et<sub>2</sub>O, <b>5c</b>∙¼H<sub>2</sub>O, and <b>6</b>∙(CH<sub>3</sub>)<sub>2</sub>SO exhibits various intra- or intermolecular O–H∙∙∙X (X = O, N, P, Cl) hydrogen contacts leading to different packing arrangements.Peter De’AthMark R. J. ElsegoodNoelia M. Sanchez-BallesterMartin B. SmithMDPI AGarticleamide groupsisomerslate-transition metalsP-ligandsphenolssecondary interactionsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6809, p 6809 (2021)
institution DOAJ
collection DOAJ
language EN
topic amide groups
isomers
late-transition metals
P-ligands
phenols
secondary interactions
Organic chemistry
QD241-441
spellingShingle amide groups
isomers
late-transition metals
P-ligands
phenols
secondary interactions
Organic chemistry
QD241-441
Peter De’Ath
Mark R. J. Elsegood
Noelia M. Sanchez-Ballester
Martin B. Smith
Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
description The solid-state behaviour of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to Pt<sup>II</sup>, have been extensively studied using single crystal X-ray crystallography. In the first library, isomeric diphosphines of the type Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub> [<b>1a</b>–<b>e</b>; Ar = C<sub>6</sub>H<sub>3</sub>(Me)(OH)] and, in the second library, amide-functionalised, isomeric ligands Ph<sub>2</sub>PCH<sub>2</sub>N{CH<sub>2</sub>C(O)NH(Ar)}CH<sub>2</sub>PPh<sub>2</sub> [<b>2a</b>–<b>e</b>; Ar = C<sub>6</sub>H<sub>3</sub>(Me)(OH)], were synthesised by reaction of Ph<sub>2</sub>PCH<sub>2</sub>OH and the appropriate amine in CH<sub>3</sub>OH, and isolated as colourless solids or oils in good yield. The non-methyl, substituted diphosphines Ph<sub>2</sub>PCH<sub>2</sub>N{CH<sub>2</sub>C(O)NH(Ar)}CH<sub>2</sub>PPh<sub>2</sub> [<b>2f</b>, Ar = 3-C<sub>6</sub>H<sub>4</sub>(OH); <b>2g</b>, Ar = 4-C<sub>6</sub>H<sub>4</sub>(OH)] and Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub> [<b>3</b>, Ar = 3-C<sub>6</sub>H<sub>4</sub>(OH)] were also prepared for comparative purposes. Reactions of <b>1a</b>–<b>e</b>, <b>2a</b>–<b>g</b>, or <b>3</b> with PtCl<sub>2</sub>(η<sup>4</sup>-cod) afforded the corresponding square-planar complexes <b>4a</b>–<b>e</b>, <b>5a</b>–<b>g</b>, and <b>6</b> in good to high isolated yields. All new compounds were characterised using a range of spectroscopic (<sup>1</sup>H, <sup>31</sup>P{<sup>1</sup>H}, FT–IR) and analytical techniques. Single crystal X-ray structures have been determined for <b>1a</b>, <b>1b</b>∙CH<sub>3</sub>OH, <b>2f</b>∙CH<sub>3</sub>OH, <b>2g</b>, <b>3</b>, <b>4b</b>∙(CH<sub>3</sub>)<sub>2</sub>SO, <b>4c</b>∙CHCl<sub>3</sub>, <b>4d</b>∙½Et<sub>2</sub>O, <b>4e</b>∙½CHCl<sub>3</sub>∙½CH<sub>3</sub>OH, <b>5a</b>∙½Et<sub>2</sub>O, <b>5b</b>, <b>5c</b>∙¼H<sub>2</sub>O, <b>5d</b>∙Et<sub>2</sub>O, and <b>6</b>∙(CH<sub>3</sub>)<sub>2</sub>SO. The free phenolic group in <b>1b</b>∙CH<sub>3</sub>OH, <b>2f</b>∙CH<sub>3</sub>OH<sub>,</sub><b>2g</b>, <b>4b</b>∙(CH<sub>3</sub>)<sub>2</sub>SO, <b>5a</b>∙½Et<sub>2</sub>O, <b>5c</b>∙¼H<sub>2</sub>O, and <b>6</b>∙(CH<sub>3</sub>)<sub>2</sub>SO exhibits various intra- or intermolecular O–H∙∙∙X (X = O, N, P, Cl) hydrogen contacts leading to different packing arrangements.
format article
author Peter De’Ath
Mark R. J. Elsegood
Noelia M. Sanchez-Ballester
Martin B. Smith
author_facet Peter De’Ath
Mark R. J. Elsegood
Noelia M. Sanchez-Ballester
Martin B. Smith
author_sort Peter De’Ath
title Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
title_short Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
title_full Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
title_fullStr Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
title_full_unstemmed Low-Dimensional Architectures in Isomeric <i>cis</i>-PtCl<sub>2</sub>{Ph<sub>2</sub>PCH<sub>2</sub>N(Ar)CH<sub>2</sub>PPh<sub>2</sub>} Complexes Using Regioselective-N(Aryl)-Group Manipulation
title_sort low-dimensional architectures in isomeric <i>cis</i>-ptcl<sub>2</sub>{ph<sub>2</sub>pch<sub>2</sub>n(ar)ch<sub>2</sub>pph<sub>2</sub>} complexes using regioselective-n(aryl)-group manipulation
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/121a97a7c71d47f38ce993cbb44ea037
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AT noeliamsanchezballester lowdimensionalarchitecturesinisomericicisiptclsub2subphsub2subpchsub2subnarchsub2subpphsub2subcomplexesusingregioselectivenarylgroupmanipulation
AT martinbsmith lowdimensionalarchitecturesinisomericicisiptclsub2subphsub2subpchsub2subnarchsub2subpphsub2subcomplexesusingregioselectivenarylgroupmanipulation
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