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Record W2042935274 · doi:10.1039/b703368k

Chirality transfer through hydrogen-bonding: Experimental and ab initio analyses of vibrational circular dichroism spectra of methyl lactate in water

2007· article· en· W2042935274 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenuePhysical Chemistry Chemical Physics · 2007
Typearticle
Languageen
FieldChemistry
TopicMolecular spectroscopy and chirality
Canadian institutionsUniversity of Alberta
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsVibrational circular dichroismHydrogen bondChemistryPolarizable continuum modelMoleculeChirality (physics)PopulationCircular dichroismSpectral lineAb initioInfrared spectroscopyComputational chemistryCrystallographySolvationOrganic chemistry

Abstract

fetched live from OpenAlex

The infrared vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra of methyl lactate were measured in the 1000-1800 cm(-1) region in the CCl(4) and H(2)O solvents, respectively. In particular, the chirality transfer effect, i.e. the H-O-H bending bands of the achiral water subunits that are hydrogen-bonded to the methyl lactate molecule exhibit substantial VCD strength, was detected experimentally. A series of density functional theory calculations using B3PW91 and B3LYP functionals with 6-311++G(d,p) and aug-cc-pVTZ basis sets were carried out to simulate the VA and VCD spectra of the methyl lactate monomer and the methyl lactate-(H(2)O)(n) complexes with n = 1, 2, 3. The population weighted VA and VCD spectra of the methyl lactate monomer are in good agreement with the experimental spectra in CCl(4). Implicit polarizable continuum model was found to be inadequate to account for the hydrogen-bonding effect in the observed VA and VCD spectra in H(2)O. The methyl lactate-(H(2)O)(n) complexes with n = 1, 2, 3 were used to model the explicit hydrogen-bonding. The population weighted VA and VCD spectra of the methyl lactate-H(2)O binary complex are shown to capture the main spectral features in the observed spectra in aqueous solution. The theoretical modeling shows that the extent of chirality transfer depends sensitively on the specific binding sites taken by the achiral water molecules. The observation of chirality transfer effect opens a new spectral window to detect and to model the hydrogen-bonding solvent effect on VCD spectra of chiral molecules.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.012
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.030
GPT teacher head0.323
Teacher spread0.293 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it