Platinum(II)‐Mediated Double Coupling of 2,3‐Diphenylmaleimidine with Nitrile Functionalities To Give Annulated Pentaazanonatetraenate (PANT) Systems

Ivanov, Daniil M.; Gushchin, Pavel V.; Novikov, Alexander S.; Avdontceva, Margarita S.; Zolotarev, Andrey A.; Старова, Галина Л.; Chen, Yi-Ting; Liu, Shih-Hung; Chou, Pi‐Tai; Kukushkin, Vadim Yu.

doi:10.1002/ejic.201501398

Cited by 6 publications

(4 citation statements)

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“…In accord with our recently reported procedure, 29 the PANT platinum(II) chloride complexes were synthesized by coupling of the nitrile ligands in trans-[PtCl 2 (RCN) 2 ] with 2,3-diphenylmaleimidine (molar ratio 1:2, CH 2 Cl 2 , RT) followed by purification of the formed [PtCl(PANT)] complexes by column chromatography.…”

Section: Resultsmentioning

confidence: 99%

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A family of heterotetrameric clusters of chloride species and halomethanes held by two halogen and two hydrogen bonds

et al. 2016

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Two previously reported 1, 3,5,7,3,6, chloride platinum(II) complexes [PtCl{HN=C(R)N=CN[C(Ph)=C(Ph)]C=NC(R)=NH}] (R = t Bu 1, Ph 2) form solvates with halomethanes 1•1¼CH2Cl2, 1•1⅖CH2Br2, and 2•CHCl3. All these species featuring novel complex-solvent heterotetrameric clusters, where the structural units are linked by simultaneous two C-X•••Cl-Pt (X = Cl, Br) halogen and two C-H•••Cl-Pt hydrogen bonds. The geometric parameters of these weak interactions were determined by single-crystal XRD, and the nature of XB's and HB's in the clusters were studied for the isolated model systems (1)2•(CH2Cl2)2, (1)2•(CH2Br2)2, and (2)2•(CHCl3)2 by DFT calculations and Bader's AIM analysis. The evaluated energies of the weak interactions are in the range 0.9-3.0 kcal/mol. The XB's and HB's in the reported clusters are cooperative. In the cases of (1)2•(CH2Cl2)2 and (1)2•(CH2Br2)2, the contribution of HB's to the stabilization of the system is dominant, whereas for (2)2•(CHCl3)2 contributions of both types of non-covalent interactions are almost the same. Crystal packing and other forces such as, e.g. dipole-dipole interactions, also affect the formation of the clusters.

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Section: Resultsmentioning

confidence: 99%

“…Compounds 1 and 2 were synthesized as previously described. 29 Solvents were obtained from commercial sources and used as received. Crystals 1•1¼CH 2 Cl 2 , 1•1⅖CH 2 Br 2 , and 2•CHCl 3 were grown by slow evaporation of 1 and 2 solutions in corresponding solvents.…”

Section: Methodsmentioning

confidence: 99%

A family of heterotetrameric clusters of chloride species and halomethanes held by two halogen and two hydrogen bonds

et al. 2016

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“…In ref. [8], interesting photophysical properties of symmetric pentaaza-nonatetraenoate (PANT) ring systems, which are potentially useful in medicinal chemistry, were discussed and analyzed using the time-dependent density functional theory (TD-DFT) at the B3LYP/LANL2DZ (Pt) and B3LYP/6-31G(d,p) (H, C, N, F, and Cl) levels of theory with dichloromethane used as the solvent environment, and a detailed analysis of the corresponding frontier molecular orbitals for the lower-lying transition was conducted. In ref.…”

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“…In [7], based on DFT calculations at the CPCM-B3LYP/6-311+G(d,p)//gas-B3LYP/6-31G(d) level of theory, the Pd II -mediated integration of isocyanate and azide ions was found to occur via a formal 1,3-dipolar cycloaddition between RNC ligands and uncomplexed azide. In [8], interesting photophysical properties of symmetric pentaaza-nonatetraenoate (PANT) ring systems, which are potentially useful in medicinal chemistry, were discussed and analyzed using the time-dependent density functional theory (TD-DFT) at the B3LYP/LANL2DZ (Pt) and B3LYP/6-31G(d,p) (H, C, N, F, and Cl) levels of theory with dichloromethane used as the solvent environment, and a detailed analysis of the corresponding frontier molecular orbitals for the lower-lying tran-Chemistry and Materials Science computational and quantum chemistry computational statistics artificial intelligence machine learning neural networks predictive analytics data mining and data science mechanical, thermal, structural, electric, magnetic, and optical properties of of compounds…”

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Computer Modeling and Machine Learning in Chemistry and Materials Science: From Properties and Reactions of Small Organic and Inorganic Molecules to the Smart Design of Polymers and Composites

Novikov

2023

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Computer modeling, machine learning, and artificial intelligence are currently considered cutting-edge topics in chemistry and materials science. The application of information technologies in natural sciences can help researchers collect big data and understand patterns that are not obvious to humans. In this perspective, I would like to highlight the recent achievements of our research group and other researchers in relation to computer modeling and machine learning in chemistry and materials science.

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Diiodomethane as a halogen bond donor toward metal-bound halides

et al. 2017

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A 1, 3,5,7,3,6, chloride platinumĲII) complex (1) was obtained via the metal-mediated double coupling of 2,3-diphenylmaleimidine with both nitrile ligands in trans-Compound 1 was then co-crystallized with diiodomethane forming solvate 1·½CH 2 I 2 . The XRD experiment reveals that this solvate displays the halogen bonds H 2 C(I)-I⋯Cl-Pt and hydrogen bonds I 2 C(H)-H⋯Cl-Pt, which join two complex and one CH 2 I 2 molecules in a heterotrimeric supramolecular cluster. Inspection of the CCDC database reveals only one example of the halogen bond H 2 C(I)-I⋯I-Pt between the CH 2 I 2 molecule and metal-coordinated halide in the structure of VEMWOA. In VEMWOA, CH 2 I 2 serves solely as a halogen bond donor with no hydrogen bond contribution. Results of the Hirshfeld surface analysis and DFT calculations (M06/DZP-DKH level of theory) followed by topological analysis of the electron density distribution within the formalism of Bader's theory (QTAIM method) for both 1·½CH 2 I 2 and VEMWOA confirmed the formation of these weak interactions. The evaluated energies of halogen bonds involving CH 2 I 2 are in the 2.2-2.8 kcal mol −1 range.

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Platinum(II)‐Mediated Double Coupling of 2,3‐Diphenylmaleimidine with Nitrile Functionalities To Give Annulated Pentaazanonatetraenate (PANT) Systems

Cited by 6 publications

References 69 publications

A family of heterotetrameric clusters of chloride species and halomethanes held by two halogen and two hydrogen bonds

A family of heterotetrameric clusters of chloride species and halomethanes held by two halogen and two hydrogen bonds

Computer Modeling and Machine Learning in Chemistry and Materials Science: From Properties and Reactions of Small Organic and Inorganic Molecules to the Smart Design of Polymers and Composites

Diiodomethane as a halogen bond donor toward metal-bound halides

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