@article{f368216c0b3c4a24a2ebb336838076ca,
title = "Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals",
abstract = "The analysis of the structures of low-energy conformers of different α-haloacetals reveals changes in bond lengths and geometries that correspond to stabilizing orbital interactions that contribute to the ground-state structures of these systems. Several factors, including the electron-donating and electron-accepting abilities of the substituents on the ring, affect the degree of the electronic interactions in these carbohydrate-like systems. The presence of an α-halogen atom that can participate in hyperconjugation has been shown to contribute to the structural characteristics of the low-energy conformer. The experimental evidence is supported by natural bond order (NBO) analysis to identify the types of interactions and to assess their relative importance.",
author = "Demkiw, {Krystyna M.} and Hu, {Chunhua T.} and Woerpel, {K. A.}",
note = "Funding Information: This research was supported by the National Institutes of Health, National Institute of General Medical Sciences (1R01GM129286). K.M.D. acknowledges the NYU Department of Chemistry for support in the form of a Margaret Strauss Kramer Fellowship. The authors acknowledge NYU{\textquoteright}s Shared Instrumentation Facility and the support provided by NSF award CHE-01162222 and NIH award S10-OD016343. The authors thank Dr. Chin Lin (NYU) for his assistance with NMR spectroscopy and mass spectroscopy. The authors thank Alexandra Dillon (NYU) for her attempts to encapsulate oils in a crystalline framework suitable for analysis by X-ray diffraction. The authors thank Alya Arabi (United Arab Emirates University) and Shereef Elmetwaly (NYU) for insightful discussions. The X-ray facility at NYU was supported partially by the National Science Foundation (NSF) Chemistry Research Instrumentation and Facilities Program (CHE-0840277) and Materials Research Science and Engineering Center (MRSEC) Program (DMR-1420073). Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",
year = "2022",
month = apr,
day = "15",
doi = "10.1021/acs.joc.2c00148",
language = "English (US)",
volume = "87",
pages = "5315--5327",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "8",
}