Synthesis, molecular structure and vibrational spectra of
1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones

J 2015

Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones

BABJAKOVÁ, Eva, Lenka DASTYCHOVÁ, Barbora HANULÍKOVÁ, Ivo KUŘITKA, Marek NEČAS et. al.

Základní údaje

Originální název

Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones

Autoři

BABJAKOVÁ, Eva, Lenka DASTYCHOVÁ, Barbora HANULÍKOVÁ, Ivo KUŘITKA, Marek NEČAS (203 Česká republika, domácí), Hana VAŠKOVÁ a Robert VÍCHA

Vydání

Journal of Molecular Structure, Amsterdam, ELSEVIER SCIENCE BV, 2015, 0022-2860

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Nizozemské království

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Full Text

Impakt faktor

Impact factor: 1.780

Kód RIV

RIV/00216224:14310/15:00112209

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1016/j.molstruc.2014.12.074

UT WoS

000350075100025

Klíčová slova anglicky

1-Adamantyl; 1.3-Diones; Vibration spectroscopy; X-ray; DFT calculations

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 9. 1. 2020 16:17, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

The interest in the oxo-enol tautomerism of 1,3-dioxo compounds is justified by their usefulness in many synthetic fields. A series of new 1,3-bis(1-adamantyl)propan-1,3-diones with a variably substituted phenyl ring at the C2 position was prepared either by the reaction of an appropriate Grignard reagent with adamatane-1-carbonyl chloride or by SEAr on the unsubstituted 1,3-bis(1-adamanty1)-2-phenylpropan-1,3-dione. In addition to the single crystal X-ray diffraction analysis of three of the prepared compounds, the experimental H-1 and C-13 NMR, IR and Raman spectroscopic data were assigned and compared to those obtained by DFT computations. In the solid state, the syn-dioxo forms were exclusively observed, which are shown to also predominate in CHCl3 solutions. The analysis of the Hirshfeld surface revealed that H center dot center dot center dot H and O center dot center dot center dot H contacts dominate the intermolecular interactions in the solid state, whereas it pi center dot center dot center dot pi stacking plays a marginal role.

Citovat

BABJAKOVÁ, Eva, Lenka DASTYCHOVÁ, Barbora HANULÍKOVÁ, Ivo KUŘITKA, Marek NEČAS, Hana VAŠKOVÁ a Robert VÍCHA. Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones. Journal of Molecular Structure. Amsterdam: ELSEVIER SCIENCE BV, 2015, roč. 1085, APR, s. 207-214. ISSN 0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2014.12.074.

@article{1601281,
   author = {Babjaková, Eva and Dastychová, Lenka and Hanulíková, Barbora and Kuřitka, Ivo and Nečas, Marek and Vašková, Hana and Vícha, Robert},
   article_location = {Amsterdam},
   article_number = {APR},
   doi = {http://dx.doi.org/10.1016/j.molstruc.2014.12.074},
   keywords = {1-Adamantyl; 1.3-Diones; Vibration spectroscopy; X-ray; DFT calculations},
   language = {eng},
   issn = {0022-2860},
   journal = {Journal of Molecular Structure},
   title = {Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones},
   url = {https://www.sciencedirect.com/science/article/pii/S0022286014012800},
   volume = {1085},
   year = {2015}
}

TY  - JOUR
ID  - 1601281
AU  - Babjaková, Eva - Dastychová, Lenka - Hanulíková, Barbora - Kuřitka, Ivo - Nečas, Marek - Vašková, Hana - Vícha, Robert
PY  - 2015
TI  - Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones
JF  - Journal of Molecular Structure
VL  - 1085
IS  - APR
SP  - 207-214
EP  - 207-214
PB  - ELSEVIER SCIENCE BV
SN  - 00222860
KW  - 1-Adamantyl
KW  - 1.3-Diones
KW  - Vibration spectroscopy
KW  - X-ray
KW  - DFT calculations
UR  - https://www.sciencedirect.com/science/article/pii/S0022286014012800
L2  - https://www.sciencedirect.com/science/article/pii/S0022286014012800
N2  - The interest in the oxo-enol tautomerism of 1,3-dioxo compounds is justified by their usefulness in many synthetic fields. A series of new 1,3-bis(1-adamantyl)propan-1,3-diones with a variably substituted phenyl ring at the C2 position was prepared either by the reaction of an appropriate Grignard reagent with adamatane-1-carbonyl chloride or by SEAr on the unsubstituted 1,3-bis(1-adamanty1)-2-phenylpropan-1,3-dione. In addition to the single crystal X-ray diffraction analysis of three of the prepared compounds, the experimental H-1 and C-13 NMR, IR and Raman spectroscopic data were assigned and compared to those obtained by DFT computations. In the solid state, the syn-dioxo forms were exclusively observed, which are shown to also predominate in CHCl3 solutions. The analysis of the Hirshfeld surface revealed that H center dot center dot center dot H and O center dot center dot center dot H contacts dominate the intermolecular interactions in the solid state, whereas it pi center dot center dot center dot pi stacking plays a marginal role.
ER  -

BABJAKOVÁ, Eva, Lenka DASTYCHOVÁ, Barbora HANULÍKOVÁ, Ivo KUŘITKA, Marek NEČAS, Hana VAŠKOVÁ a Robert VÍCHA. Synthesis, molecular structure and vibrational spectra of 1,3-bis(1-adamantyl)-2-phenylpropan-1,3-diones. \textit{Journal of Molecular Structure}. Amsterdam: ELSEVIER SCIENCE BV, 2015, roč.~1085, APR, s.~207-214. ISSN~0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2014.12.074.

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