Synthesis, Molecular, and Crystal Structure of Tris(2-carbamoylmethoxyphenyl)phosphine Oxide
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hesis, Molecular, and Crystal Structure of Tris(2-carbamoylmethoxyphenyl)phosphine Oxide T. V. Baulinaa, I. Yu. Kudryavtseva,*, A. V. Artem’evb, I. Yu. Bagryanskayac, M. P. Pasechnika, and V. K. Brela a Nesmeyanov
Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, 119991 Russia Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090 Russia c Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090 Russia *e-mail: [email protected] b Nikolaev
Received June 17, 2020; revised June 17, 2020; accepted June 30, 2020
Abstract—New tripodal ligand, tris(2-carbamoylmethoxyphenyl)phosphine oxide, has been synthesized via the alkylation of tris(2-hydroxyphenyl)phosphine oxide with chloroacetamide. The ligand structure has been studied by means of IR and NMR (1H, 31P) spectroscopy as well as X-ray diffraction. Keywords: tripodal ligand, tris(2-carbamoylmethoxyphenyl)phosphine oxide, crystal and molecular structure
DOI: 10.1134/S1070363220100059 Tripodal ligands form a promising group of organic complex-forming agents, versatile structure of which affords the compounds capable of binding the substrates of different classes. The ligands containing carbamoyl groups can form strong complexes with the salts of dand f-elements and can be used as extracting agents for recovery and separation of valuable metals as well as for reprocessing of spent nuclear fuel [1–5]. Tripodal ligands bearing functional proton-donor groups can form complexes with anions [6–9]. Tuning of the tripodal ligands structure has allowed ionophores for ion-selective electrodes and optical sensors for metal ions [10–12]. Tripodal ligands can bind neutral organic molecules, for example carboxylic acids [13] and carbohydrates [14] and act as sensors, receptors, and artificial enzymes. The so-called propeller ligands based on pyramidal organic compounds with three aryl substituents and functional groups in the side chain form a special type of tripodal ionophores. These ligands include the derivatives of triarylmethane, triarylamine, triarylphosphine, and triarylphosphine oxide. The most stable conformation of such molecules corresponds to the geometry of asymmetric propeller with the ortho-substituents in the benzene rings being oriented to the same direction (Scheme 1). Such geometry allows the preparation of ionophores with the coordinating moieties in the side chains being spatially close and hence prone to the formation of multiple bonds
with the guest ions and molecules with minor change of the ligand conformation [15–17]. In contrast to the extracting agents used in hydrometallurgy, which should exhibit significant lipophilicity and low solubility in water, sometimes it is desirable to obtain water-soluble ligands and complexes, for example, in industries utilizing water as the cheapest and the most available solvent. Solubility in water is a prerequisite for the ligands and their complexes suitable for application in physiologi
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