Matches in SemOpenAlex for { <https://semopenalex.org/work/W2092190687> ?p ?o ?g. }
- W2092190687 endingPage "4873" @default.
- W2092190687 startingPage "4865" @default.
- W2092190687 abstract "By reacting flexible and optically transparent in UV-vis molecules such as 1,2-, syn- and anti-1,3-diols, 1,3-sulfanylalcohols of known absolute configuration (AC) with fluorenone dimethyl acetal, the corresponding ketals are obtained. They are conformationally well-defined (only one conformer in most cases) compounds exhibiting medium-high optical rotation (OR) values, which are independent of the solvent, and electronic circular dichroism (ECD) spectra, which show several (up to five) Cotton effects in the 350-200 nm range due to valence shell pi-->pi* transitions. These features allow simulation of the chiroptical properties of these compounds at the TDDFT/B3LYP/6-31G* level of theory to obtain, using the known ACs of these compounds, a satisfactory reproduction of the OR values (sign and order of magnitude; quantitatively, the predicted values are twice the experimental ones), and a more than satisfactory reproduction of the ECD spectra (sign, intensity, and position of the lowest-energy four Cotton effects) for all the compounds studied. Therefore, this approach can be used to assign the AC of such flexible molecules, in particular, syn-1,3-diols, which are important substrates in organic synthesis and for which nonempirical methods of AC assignment have not been devised so far. Furthermore, since the fluorene chromophore leads to the presence of several Cotton effects from, say, 350 to 200 nm, their correct simulation of sign, intensity, and position is a guarantee of the correct assignment of AC: in this way, ECD spectroscopy gains the same advantages of VCD spectroscopy, that is, the need of reproducing many ECD bands and then a solid guarantee of a correct AC assignment." @default.
- W2092190687 created "2016-06-24" @default.
- W2092190687 creator A5019823749 @default.
- W2092190687 creator A5048214433 @default.
- W2092190687 creator A5058257850 @default.
- W2092190687 creator A5059666829 @default.
- W2092190687 creator A5064837553 @default.
- W2092190687 date "2008-06-12" @default.
- W2092190687 modified "2023-09-30" @default.
- W2092190687 title "A Chemical/Computational Approach to the Determination of Absolute Configuration of Flexible and Transparent Molecules: Aliphatic Diols As a Case Study" @default.
- W2092190687 cites W1582849918 @default.
- W2092190687 cites W1964830845 @default.
- W2092190687 cites W1966569521 @default.
- W2092190687 cites W1967177826 @default.
- W2092190687 cites W1967458361 @default.
- W2092190687 cites W1968508897 @default.
- W2092190687 cites W1968853883 @default.
- W2092190687 cites W1972166478 @default.
- W2092190687 cites W1973984360 @default.
- W2092190687 cites W1978309006 @default.
- W2092190687 cites W1978589749 @default.
- W2092190687 cites W1986788583 @default.
- W2092190687 cites W1990377303 @default.
- W2092190687 cites W1993690918 @default.
- W2092190687 cites W1995343241 @default.
- W2092190687 cites W1997151511 @default.
- W2092190687 cites W1997725714 @default.
- W2092190687 cites W1998759411 @default.
- W2092190687 cites W2000201317 @default.
- W2092190687 cites W2001892418 @default.
- W2092190687 cites W2005995289 @default.
- W2092190687 cites W2006869357 @default.
- W2092190687 cites W2007468072 @default.
- W2092190687 cites W2013863268 @default.
- W2092190687 cites W2014864684 @default.
- W2092190687 cites W2015183186 @default.
- W2092190687 cites W2018144398 @default.
- W2092190687 cites W2018537588 @default.
- W2092190687 cites W2018912013 @default.
- W2092190687 cites W2019235763 @default.
- W2092190687 cites W2019406315 @default.
- W2092190687 cites W2019887434 @default.
- W2092190687 cites W2022068490 @default.
- W2092190687 cites W2029053687 @default.
- W2092190687 cites W2029223361 @default.
- W2092190687 cites W2029967388 @default.
- W2092190687 cites W2032529064 @default.
- W2092190687 cites W2033004698 @default.
- W2092190687 cites W2033134153 @default.
- W2092190687 cites W2035821946 @default.
- W2092190687 cites W2035871617 @default.
- W2092190687 cites W2037026428 @default.
- W2092190687 cites W2038056583 @default.
- W2092190687 cites W2040067453 @default.
- W2092190687 cites W2040981470 @default.
- W2092190687 cites W2042174834 @default.
- W2092190687 cites W2043289059 @default.
- W2092190687 cites W2052799234 @default.
- W2092190687 cites W2053235603 @default.
- W2092190687 cites W2056346122 @default.
- W2092190687 cites W2058095473 @default.
- W2092190687 cites W2059076534 @default.
- W2092190687 cites W2059403560 @default.
- W2092190687 cites W2063707560 @default.
- W2092190687 cites W2064985841 @default.
- W2092190687 cites W2067497467 @default.
- W2092190687 cites W2067616943 @default.
- W2092190687 cites W2069611861 @default.
- W2092190687 cites W2069876255 @default.
- W2092190687 cites W2069901076 @default.
- W2092190687 cites W2071109517 @default.
- W2092190687 cites W2071505798 @default.
- W2092190687 cites W2071746010 @default.
- W2092190687 cites W2074645979 @default.
- W2092190687 cites W2077182652 @default.
- W2092190687 cites W2077739282 @default.
- W2092190687 cites W2078296075 @default.
- W2092190687 cites W2083159433 @default.
- W2092190687 cites W2083622852 @default.
- W2092190687 cites W2084167813 @default.
- W2092190687 cites W2087614231 @default.
- W2092190687 cites W2091765952 @default.
- W2092190687 cites W2091951817 @default.
- W2092190687 cites W2092745664 @default.
- W2092190687 cites W2092751380 @default.
- W2092190687 cites W2092787673 @default.
- W2092190687 cites W2097457838 @default.
- W2092190687 cites W2111077672 @default.
- W2092190687 cites W2111245131 @default.
- W2092190687 cites W2124380804 @default.
- W2092190687 cites W2133205577 @default.
- W2092190687 cites W2144692952 @default.
- W2092190687 cites W2155082091 @default.
- W2092190687 cites W2170612562 @default.
- W2092190687 cites W2318426697 @default.
- W2092190687 cites W2489106386 @default.
- W2092190687 cites W2870580275 @default.
- W2092190687 cites W2914218443 @default.