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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F15%3A00112209" target="_blank" >RIV/00216224:14310/15:00112209 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/70883521:28140/15:43873054 RIV/70883521:28610/15:43873054 RIV/70883521:28110/15:43873054

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0022286014012800" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022286014012800</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2014.12.074" target="_blank" >10.1016/j.molstruc.2014.12.074</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

1872-8014

Svazek periodika

1085

Číslo periodika v rámci svazku

APR

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

207-214

Kód UT WoS článku

000350075100025

EID výsledku v databázi Scopus

2-s2.0-84921635502