How important are the intermolecular hydrogen bonding interactions in methanol solvent for interpreting the chiroptical properties?

Polavarapu, Prasad L.; Santoro, Ernesto; Covington, Cody L.; Johnson, Jordan L.; Puente, Andrew R.; Schley, Nathan D.; Kallingathodi, Zabeera; Prakasan, Prasanth C.; Haleema, Simimole; Thomas, Annu Anna; Ibnusaud, Ibrahim

doi:10.1016/j.saa.2020.119094

Cited by 16 publications

(23 citation statements)

References 52 publications

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“…There are some differences among the magnitudes of predicted specific rotations for ent ‐ 2A , 2B , 2C , and ent ‐ 2D (Figure 2), and the magnitudes predicted for 2C are closer to the experimental magnitudes. Quantitative analysis (see Equation ) 19 indicates that the RMSD values for ent ‐ 2A , 2B , 2C , and ent ‐ 2D are, respectively, 272, 320, 244, and 370. Based on these RMSD values, 2C is the preferred diastereomer for the AC assignment.…”

Section: Resultsmentioning

confidence: 99%

“…The specific optical rotation (SOR) predicted at 633, 589, 546, 436, 405, and 365 nm was used to generate ORD. The quantitative comparison between experimental and calculated ORD is obtained 19 by calculating the root mean square deviation (RMSD) as follows:

RMSD = \sqrt{\sum_{i} \frac{{((),,, Yi, calc ‐ Yi, obs)}^{2}}{N}}

where Y i,calc and Y i,obs are, respectively, the calculated and experimental SORs at i th wavelength and N is the number of discrete wavelength data points and the summation runs over discrete wavelength data points.…”

Section: Methodsmentioning

confidence: 99%

“…CDSpecTech is a freely available program which directly reads the output files from Gaussian program and simulates the chiroptical spectra. In addition, this program calculates the above mentioned similarity values as a function of frequency/wavelength scale factor and incorporates various options, as detailed by Polavarapu et al 19 and Covington et al 21 …”

Section: Methodsmentioning

confidence: 99%

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Absolute configuration of seco‐eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4‐O‐acetyl derivative

et al. 2021

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Sesquitepenoids inuloxins A–D, belonging to different subgroups, were isolated from Dittrichia viscosa and showed potential biocontrol of some parasitic plants as Pelipanche, Orobanche, and Cuscuta species. The absolute configurations of the first three inuloxins A–C were previously determined by using experimental and computational chiroptical spectroscopic methods. The absolute configuration of inuloxin D remains to be established. The bioactive inuloxin E, closely related to inuloxin D, was recently isolated from the same plant organic extract. The same relative configuration of inuloxin D was assigned to inuloxin E by comparison of their NMR spectroscopic data. The absolute configurations of inuloxin D and inuloxin E are suggested in this work by analysis of the experimental and predicted chiroptical properties of the 4‐O‐acetyl derivative of inuloxin D.

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Section: Resultsmentioning

confidence: 99%

RMSD = \sqrt{\sum_{i} \frac{{((),,, Yi, calc ‐ Yi, obs)}^{2}}{N}}

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Absolute configuration of seco‐eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4‐O‐acetyl derivative

et al. 2021

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“…The absolute configuration of molecular structures of various analogs of crispine A 174 and 176 were determined, and studied employing chiroptical spectroscopic studies, and was further confirmed using the data from single-crystal XRD. [84,85]…”

Section: Enantiopure Crispine a From Diastereomeric Scaffolds -Garcinia And Hibiscus Acidsmentioning

confidence: 99%

Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

et al. 2021

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As a naturally occurring small-molecule, various optical isomers of chiral pyrrolo[2,1-a]isoquinoline alkaloid crispine A represent a potential class of chiral molecules in contemporary organic chemistry, and possess diverse biological activities. The range of pharmacological activities include antidepressant, antiplatelet, antileukemic, and anticancer activities. This review provides an overview of the literature on the strategies, employed in the synthesis of crispine A in their racemic and enantiopure forms via Bischler-Napieralski cyclization, Pictet-Spengler cyclization, N-Alkylation/Acylation-cyclization, Oxidative cyclization, and Asymmetric hydrogenation in the period of 1931-2021. This study accentuates the need for the developing more effective synthesis, and search for involved biological applications for the pyrroloisoquinoline class of natural product. Attention has been drawn towards the use of relatively less documented but easily accessible naturally occurring diastereomeric scaffolds namely, garcinia and hibiscus acids. These lactones obtained from (+)and (À )-2-hydroxycitric acids bearing chemically amenable functional groups are investigated as an ideal choice for the enantiopure synthesis of the (À )-(R)-and (+)-(S)-Crispine A structural frame work.

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“…47 Explicit solvation was not even necessary to determine the absolute configuration of a cyclic diol in methanol, which was treated as a continuum. 48 We have recently discussed the influence of solvation on the IR absorption and VCD spectrum of (1S,2S)-trans-1-amino-2indanol (trans-AI), a stereomer of cis-AI. Static calculations resting on the cluster-in-the-liquid model were assessed by comparison with first principles and force fields molecular dynamics descriptions of solvation.…”

Section: Introductionmentioning

confidence: 99%

Competition between inter and intramolecular hydrogen bond evidenced by vibrational circular dichroism spectroscopy: The case of (1S,2R)‐(−)‐cis‐1‐amino‐2‐indanol

Barbu‐Debus

Zehnacker‐Rentien

2021

Chirality

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How important are the intermolecular hydrogen bonding interactions in methanol solvent for interpreting the chiroptical properties?

Cited by 16 publications

References 52 publications

Absolute configuration of seco‐eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4‐O‐acetyl derivative

Absolute configuration of seco‐eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4‐O‐acetyl derivative

Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

Competition between inter and intramolecular hydrogen bond evidenced by vibrational circular dichroism spectroscopy: The case of (1S,2R)‐(−)‐cis‐1‐amino‐2‐indanol

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