Polymorphism and Peroxomorphism in Peroxosolvates of Zwitterionic Sulfonic Acids: Features of H-Bonding and Crystal Packing

Bezzubov, Stanislav I.; Yakushev, Ilya A.; Medvedev, Alexander G.; Prikhodchenko, Petr V.; Churakov, Andrei V.

doi:10.1021/acs.cgd.3c00656

Crystal Growth & Design

2023

DOI: 10.1021/acs.cgd.3c00656

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Polymorphism and Peroxomorphism in Peroxosolvates of Zwitterionic Sulfonic Acids: Features of H-Bonding and Crystal Packing

Stanislav I. Bezzubov,

Ilya A. Yakushev,

Alexander G. Medvedev

et al.

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2024

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Cited by 3 publications

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Polymorphism of triphenylantimony(V) bis-cumylperoxide

Mayorov,

Egorov,

Medvedev

et al. 2024

Struct Chem

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Polymorphism of triphenylantimony(V) bis-cumylperoxide

Mayorov,

Egorov,

Medvedev

et al. 2024

Struct Chem

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Three peroxomorphic H₂O₂ adducts of antibiotic furacin: the first cases of 2D hydrogen-bonded peroxide layers and concerted flip-flop hydrogen disorder of peroxide species

Churakov

2024

CrystEngComm

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Crystal Structures of Sulfobetaine-8 Solvates: Bend Hydrophobic Chains and Doubly Charge-Assisted Hydrogen Bonds N+CH⋯−O3S

Churakov,

Anokhin,

Kalle

et al. 2024

Crystals

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Three novel solvatomorphs (C13H29NO3S•CH3OH, 1; C13H29NO3S•0.113(H2O), 2; C13H29NO3S•0.038(H2O), 3) of zwitterionic sulfobetaine-8 were obtained and their structures were determined using single-crystal X-Ray diffraction. In all cases dimethyl–amino substituted hydrophobic chains -(CH2)3-N+Me2-(CH2)7-Me exhibit kinks at nitrogen atoms resulted from strong intra- and intermolecular CH⋯O hydrogen bonds between negatively charged sulfonic anion -O3S- and positively charged tetraalkylammonium fragments. Periodic (solid state) DFT calculations for structure 1 showed that the energy of the intermolecular hydrogen bonds CH…O is very high, at about 17 kJ/mol. In hydrates 2 and 3, water molecules play the structure-forming role since they interconnect hydrophobic layers by HOH…-O3S hydrogen bonds. The location of only partially occupied water molecules in the interlayer space leads to low stability of both crystals 2 and 3 in open air.

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Polymorphism and Peroxomorphism in Peroxosolvates of Zwitterionic Sulfonic Acids: Features of H-Bonding and Crystal Packing

Cited by 3 publications

References 96 publications

Polymorphism of triphenylantimony(V) bis-cumylperoxide

Polymorphism of triphenylantimony(V) bis-cumylperoxide

Three peroxomorphic H₂O₂ adducts of antibiotic furacin: the first cases of 2D hydrogen-bonded peroxide layers and concerted flip-flop hydrogen disorder of peroxide species

Crystal Structures of Sulfobetaine-8 Solvates: Bend Hydrophobic Chains and Doubly Charge-Assisted Hydrogen Bonds N+CH⋯−O3S

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Polymorphism and Peroxomorphism in Peroxosolvates of Zwitterionic Sulfonic Acids: Features of H-Bonding and Crystal Packing

Cited by 3 publications

References 96 publications

Polymorphism of triphenylantimony(V) bis-cumylperoxide

Polymorphism of triphenylantimony(V) bis-cumylperoxide

Three peroxomorphic H2O2 adducts of antibiotic furacin: the first cases of 2D hydrogen-bonded peroxide layers and concerted flip-flop hydrogen disorder of peroxide species

Crystal Structures of Sulfobetaine-8 Solvates: Bend Hydrophobic Chains and Doubly Charge-Assisted Hydrogen Bonds N+CH⋯−O3S

Contact Info

Product

Resources

About

Three peroxomorphic H₂O₂ adducts of antibiotic furacin: the first cases of 2D hydrogen-bonded peroxide layers and concerted flip-flop hydrogen disorder of peroxide species