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Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation? / Болотин, Дмитрий Сергеевич; Новиков, Александр Сергеевич; Сысоева, Александра Александровна; Ильин, Михаил Вячеславович.

In: New Journal of Chemistry, Vol. 48, No. 29, 24.06.2024, p. 12929-12935.

Research output: Contribution to journal › Article › peer-review

Harvard

Болотин, ДС, Новиков, АС, Сысоева, АА & Ильин, МВ 2024, 'Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation?', New Journal of Chemistry, vol. 48, no. 29, pp. 12929-12935. https://doi.org/10.1039/d4nj02105c

APA

Болотин, Д. С., Новиков, А. С., Сысоева, А. А., & Ильин, М. В. (2024). Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation? New Journal of Chemistry, 48(29), 12929-12935. https://doi.org/10.1039/d4nj02105c

Vancouver

Болотин ДС, Новиков АС, Сысоева АА, Ильин МВ. Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation? New Journal of Chemistry. 2024 Jun 24;48(29):12929-12935. https://doi.org/10.1039/d4nj02105c

Author

Болотин, Дмитрий Сергеевич ; Новиков, Александр Сергеевич ; Сысоева, Александра Александровна ; Ильин, Михаил Вячеславович. / Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation?. In: New Journal of Chemistry. 2024 ; Vol. 48, No. 29. pp. 12929-12935.

BibTeX

@article{0a954e88a97d4a5a8908d93c44df826b,
title = "Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation?",
abstract = "1H NMR titration of 18-crown-6 with diphenyliodonium triflate and dibenziodolium triflate indicated that the acyclic iodine(iii)-containing species has a higher binding constant value compared with the cyclic analogue. Formation of triple associates diphenyliodonium⋯18-crown-6⋯diphenyliodonium was observed in CD3CN. DFT calculations and QTAIM analysis indicated that the acyclic iodonium salt forms a higher number of interactions with the crown ether compared with the cyclic cation, which results in the formation of triple associates. The formation of dibenziodolium⋯18-crown-6⋯dibenziodolium triple associates turned out to be energetically unfavorable, which agrees with the experimentally obtained data.",
author = "Болотин, {Дмитрий Сергеевич} and Новиков, {Александр Сергеевич} and Сысоева, {Александра Александровна} and Ильин, {Михаил Вячеславович}",
year = "2024",
month = jun,
day = "24",
doi = "10.1039/d4nj02105c",
language = "English",
volume = "48",
pages = "12929--12935",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
number = "29",

}

RIS

TY - JOUR

T1 - Halogen Bonded Associates of Iodonium Salts with 18-Crown-6: Does Structural Flexibility or Structural Rigidity of the sigma-Hole Donor Provide Efficient Substrate Ligation?

AU - Болотин, Дмитрий Сергеевич

AU - Новиков, Александр Сергеевич

AU - Сысоева, Александра Александровна

AU - Ильин, Михаил Вячеславович

PY - 2024/6/24

Y1 - 2024/6/24

N2 - 1H NMR titration of 18-crown-6 with diphenyliodonium triflate and dibenziodolium triflate indicated that the acyclic iodine(iii)-containing species has a higher binding constant value compared with the cyclic analogue. Formation of triple associates diphenyliodonium⋯18-crown-6⋯diphenyliodonium was observed in CD3CN. DFT calculations and QTAIM analysis indicated that the acyclic iodonium salt forms a higher number of interactions with the crown ether compared with the cyclic cation, which results in the formation of triple associates. The formation of dibenziodolium⋯18-crown-6⋯dibenziodolium triple associates turned out to be energetically unfavorable, which agrees with the experimentally obtained data.

AB - 1H NMR titration of 18-crown-6 with diphenyliodonium triflate and dibenziodolium triflate indicated that the acyclic iodine(iii)-containing species has a higher binding constant value compared with the cyclic analogue. Formation of triple associates diphenyliodonium⋯18-crown-6⋯diphenyliodonium was observed in CD3CN. DFT calculations and QTAIM analysis indicated that the acyclic iodonium salt forms a higher number of interactions with the crown ether compared with the cyclic cation, which results in the formation of triple associates. The formation of dibenziodolium⋯18-crown-6⋯dibenziodolium triple associates turned out to be energetically unfavorable, which agrees with the experimentally obtained data.

UR - https://www.mendeley.com/catalogue/fb7f4089-ec12-3440-836f-81bb68369fd7/

U2 - 10.1039/d4nj02105c

DO - 10.1039/d4nj02105c

M3 - Article

VL - 48

SP - 12929

EP - 12935

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 29

ER -

ID: 121427016