Frustrated and realized hydrogen bonding in 4-hydroxy-3,5- ditertbutylphenylphosphine derivatives
| dc.contributor.author | Marszaukowski, Flávia | |
| dc.contributor.author | Boeré, René T. | |
| dc.contributor.author | Wohnrath, Karen | |
| dc.date.accessioned | 2022-08-26T18:33:33Z | |
| dc.date.available | 2022-08-26T18:33:33Z | |
| dc.date.issued | 2022 | |
| dc.description | Accepted author manuscript. | en_US |
| dc.description.abstract | Synthesis and molecular and supramolecular structures of a series of triarylphosphines P(Ph)3–n{4-RO-3,5-(tBu)2-C6H2}n (n = 1, 3; R = SiMe3, H) are reported. Chemical oxidation products E=P(Ph)3–n{4-RO-3,5-(tBu)2-C6H2}n (E = O, S, and Se; n = 1, 3; R = SiMe3, H) are also reported. Crystal structures of the reported compounds were determined by single-crystal X-ray diffraction, using a Hirshfeld atom refinement with NoSpherA2 through OLEX2, which provides an average improvement in C–C bond distance precision of 35%. Phosphine basicity for the phosphines with n = 1, R = H and n = 3, R = SiMe3, H was determined using the 1JP,Se values of the respective selenides; 1JP,Se = 699 Hz for E = Se, n = 3, and X = H identifies the most basic triarylphosphine ever reported. Intermolecular interactions allow classification of the 17 structures into 4 categories: those with only dispersion-induced short contacts, those with frustration of H-bonding, those with only classic H-bonding, and those with combinations of classic and frustration of H-bonding. A “double phenol embrace” classified by an R22(4) graph set is a weak intermolecular synthon organizing lattices with 2,6-ditertbutylphenol functional groups. Classic H-bonding occurs only when E = O. | en_US |
| dc.description.peer-review | Yes | en_US |
| dc.identifier.citation | Marszaukowski, F., Boeré. R. T., & Wohnrath, K. (2022). Frustrated and realized hydrogen bonding in 4-hydroxy-3,5- ditertbutylphenylphosphine derivatives. Crystal Growth & Design, 22(4), 2512-2533. https://doi.org/10.1021/acs.cgd.2c00020 | en_US |
| dc.identifier.uri | https://hdl.handle.net/10133/6324 | |
| dc.language.iso | en_US | en_US |
| dc.publisher | ACS Publications | en_US |
| dc.publisher.department | Department of Chemistry and Biochemistry | en_US |
| dc.publisher.faculty | Arts and Science | en_US |
| dc.publisher.institution | Universidade Estadual de Ponta Grossa | en_US |
| dc.publisher.institution | University of Lethbridge | en_US |
| dc.publisher.url | https://doi.org/10.1021/acs.cgd.2c00020 | en_US |
| dc.subject | Chemical structure | en_US |
| dc.subject | Crystal structure | en_US |
| dc.subject | Group 15 compounds | en_US |
| dc.subject | H-bonding | |
| dc.subject.lcsh | Aromatic compounds | |
| dc.subject.lcsh | Selenides | |
| dc.subject.lcsh | Hydrogen bonding | |
| dc.title | Frustrated and realized hydrogen bonding in 4-hydroxy-3,5- ditertbutylphenylphosphine derivatives | en_US |
| dc.type | Article | en_US |