Loading…

On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”

An accurate crystal structure determination has evidenced a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7...O9 hydrogen bonds links the amido groups of di...

Full description

Saved in:
Bibliographic Details
Published in:Journal of physical organic chemistry 2009-05, Vol.22 (11), p.1086-n/a
Main Authors: Mugnoli, Angelo, Barone, Giampaolo, Buscemi, Silvestre, Lanza, Camilla Zaira, Pace, Andrea, Pani, Marcella, Spinelli, Domenico
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page n/a
container_issue 11
container_start_page 1086
container_title Journal of physical organic chemistry
container_volume 22
creator Mugnoli, Angelo
Barone, Giampaolo
Buscemi, Silvestre
Lanza, Camilla Zaira
Pace, Andrea
Pani, Marcella
Spinelli, Domenico
description An accurate crystal structure determination has evidenced a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7...O9 hydrogen bonds links the amido groups of different molecules, causing the formation of infinite parallel ordered chains. The effect of the DMSO solvent on the energy and charge distribution of compound 5 and on its relevant 5– anion, involved in a fully degenerate rearrangement (FDR), has been deepened by quantum-mechanical DFT calculations. The calculated energy barrier for the FDR increases in going from in vacuo to DMSO, in agreement with previsions based on the Hughes and Ingold rules concerning the nucleophilic substitution of an anionic reagent (the deprotonated amido group in the side-chain) on a neutral substrate (the 1,2,4-oxadiazole ring).
doi_str_mv 10.1002/poc.1563
format article
fullrecord <record><control><sourceid>hal</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00483243v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>oai_HAL_hal_00483243v1</sourcerecordid><originalsourceid>FETCH-hal_primary_oai_HAL_hal_00483243v13</originalsourceid><addsrcrecordid>eNqVTrtOwzAUtRBIlIfEJ3ikUl3sOIGGDQFVByQkxB7dJreNkR-V7QBh6ofAh7H2S3CBgZXp6p43ISeCjwXn2dnK1WNRnMsdMhC8LJmQZbFLBnxS5kxmku-TgxCeOE9ccTEgn_eWxhZpiL6rY-eRugWVDGqMvQajrGMFMxjbXjMxykY5c6_QKHhzGinYhrof_6LTuqcNLtGih4jUI3gPdokGbQz0dHrzMNxmq_SAVc5eUkitynQaorJLWjuzAq9CCpxjfEG0KSN0OumTbbN-V5YFpVWdBHWLRqXJ_Wb98b0i0Rrm7C9-RPYWoAMe_95DMpzePl7PWAu6WnllwPeVA1XNru6qLcZ5PpFZLp-F_I_2C6h2fUk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Mugnoli, Angelo ; Barone, Giampaolo ; Buscemi, Silvestre ; Lanza, Camilla Zaira ; Pace, Andrea ; Pani, Marcella ; Spinelli, Domenico</creator><creatorcontrib>Mugnoli, Angelo ; Barone, Giampaolo ; Buscemi, Silvestre ; Lanza, Camilla Zaira ; Pace, Andrea ; Pani, Marcella ; Spinelli, Domenico</creatorcontrib><description>An accurate crystal structure determination has evidenced a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7...O9 hydrogen bonds links the amido groups of different molecules, causing the formation of infinite parallel ordered chains. The effect of the DMSO solvent on the energy and charge distribution of compound 5 and on its relevant 5– anion, involved in a fully degenerate rearrangement (FDR), has been deepened by quantum-mechanical DFT calculations. The calculated energy barrier for the FDR increases in going from in vacuo to DMSO, in agreement with previsions based on the Hughes and Ingold rules concerning the nucleophilic substitution of an anionic reagent (the deprotonated amido group in the side-chain) on a neutral substrate (the 1,2,4-oxadiazole ring).</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.1563</identifier><language>eng</language><publisher>Wiley</publisher><ispartof>Journal of physical organic chemistry, 2009-05, Vol.22 (11), p.1086-n/a</ispartof><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://hal.science/hal-00483243$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Mugnoli, Angelo</creatorcontrib><creatorcontrib>Barone, Giampaolo</creatorcontrib><creatorcontrib>Buscemi, Silvestre</creatorcontrib><creatorcontrib>Lanza, Camilla Zaira</creatorcontrib><creatorcontrib>Pace, Andrea</creatorcontrib><creatorcontrib>Pani, Marcella</creatorcontrib><creatorcontrib>Spinelli, Domenico</creatorcontrib><title>On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”</title><title>Journal of physical organic chemistry</title><description>An accurate crystal structure determination has evidenced a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7...O9 hydrogen bonds links the amido groups of different molecules, causing the formation of infinite parallel ordered chains. The effect of the DMSO solvent on the energy and charge distribution of compound 5 and on its relevant 5– anion, involved in a fully degenerate rearrangement (FDR), has been deepened by quantum-mechanical DFT calculations. The calculated energy barrier for the FDR increases in going from in vacuo to DMSO, in agreement with previsions based on the Hughes and Ingold rules concerning the nucleophilic substitution of an anionic reagent (the deprotonated amido group in the side-chain) on a neutral substrate (the 1,2,4-oxadiazole ring).</description><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqVTrtOwzAUtRBIlIfEJ3ikUl3sOIGGDQFVByQkxB7dJreNkR-V7QBh6ofAh7H2S3CBgZXp6p43ISeCjwXn2dnK1WNRnMsdMhC8LJmQZbFLBnxS5kxmku-TgxCeOE9ccTEgn_eWxhZpiL6rY-eRugWVDGqMvQajrGMFMxjbXjMxykY5c6_QKHhzGinYhrof_6LTuqcNLtGih4jUI3gPdokGbQz0dHrzMNxmq_SAVc5eUkitynQaorJLWjuzAq9CCpxjfEG0KSN0OumTbbN-V5YFpVWdBHWLRqXJ_Wb98b0i0Rrm7C9-RPYWoAMe_95DMpzePl7PWAu6WnllwPeVA1XNru6qLcZ5PpFZLp-F_I_2C6h2fUk</recordid><startdate>20090513</startdate><enddate>20090513</enddate><creator>Mugnoli, Angelo</creator><creator>Barone, Giampaolo</creator><creator>Buscemi, Silvestre</creator><creator>Lanza, Camilla Zaira</creator><creator>Pace, Andrea</creator><creator>Pani, Marcella</creator><creator>Spinelli, Domenico</creator><general>Wiley</general><scope>1XC</scope><scope>VOOES</scope></search><sort><creationdate>20090513</creationdate><title>On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”</title><author>Mugnoli, Angelo ; Barone, Giampaolo ; Buscemi, Silvestre ; Lanza, Camilla Zaira ; Pace, Andrea ; Pani, Marcella ; Spinelli, Domenico</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-hal_primary_oai_HAL_hal_00483243v13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mugnoli, Angelo</creatorcontrib><creatorcontrib>Barone, Giampaolo</creatorcontrib><creatorcontrib>Buscemi, Silvestre</creatorcontrib><creatorcontrib>Lanza, Camilla Zaira</creatorcontrib><creatorcontrib>Pace, Andrea</creatorcontrib><creatorcontrib>Pani, Marcella</creatorcontrib><creatorcontrib>Spinelli, Domenico</creatorcontrib><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mugnoli, Angelo</au><au>Barone, Giampaolo</au><au>Buscemi, Silvestre</au><au>Lanza, Camilla Zaira</au><au>Pace, Andrea</au><au>Pani, Marcella</au><au>Spinelli, Domenico</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”</atitle><jtitle>Journal of physical organic chemistry</jtitle><date>2009-05-13</date><risdate>2009</risdate><volume>22</volume><issue>11</issue><spage>1086</spage><epage>n/a</epage><pages>1086-n/a</pages><issn>0894-3230</issn><eissn>1099-1395</eissn><abstract>An accurate crystal structure determination has evidenced a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7...O9 hydrogen bonds links the amido groups of different molecules, causing the formation of infinite parallel ordered chains. The effect of the DMSO solvent on the energy and charge distribution of compound 5 and on its relevant 5– anion, involved in a fully degenerate rearrangement (FDR), has been deepened by quantum-mechanical DFT calculations. The calculated energy barrier for the FDR increases in going from in vacuo to DMSO, in agreement with previsions based on the Hughes and Ingold rules concerning the nucleophilic substitution of an anionic reagent (the deprotonated amido group in the side-chain) on a neutral substrate (the 1,2,4-oxadiazole ring).</abstract><pub>Wiley</pub><doi>10.1002/poc.1563</doi><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0894-3230
ispartof Journal of physical organic chemistry, 2009-05, Vol.22 (11), p.1086-n/a
issn 0894-3230
1099-1395
language eng
recordid cdi_hal_primary_oai_HAL_hal_00483243v1
source Wiley-Blackwell Read & Publish Collection
title On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison between results of “in-silicon chemistry” and “lab-chemistry”
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T12%3A03%3A32IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-hal&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=On%20the%20structure%20of%203-acetylamino-5-methyl-1,2,4-oxadiazole%20and%20on%20the%20fully%20degenerate%20rearrangements%20(FDR)%20of%20its%20anion:%20a%20stimulating%20comparison%20between%20results%20of%20%E2%80%9Cin-silicon%20chemistry%E2%80%9D%20and%20%E2%80%9Clab-chemistry%E2%80%9D&rft.jtitle=Journal%20of%20physical%20organic%20chemistry&rft.au=Mugnoli,%20Angelo&rft.date=2009-05-13&rft.volume=22&rft.issue=11&rft.spage=1086&rft.epage=n/a&rft.pages=1086-n/a&rft.issn=0894-3230&rft.eissn=1099-1395&rft_id=info:doi/10.1002/poc.1563&rft_dat=%3Chal%3Eoai_HAL_hal_00483243v1%3C/hal%3E%3Cgrp_id%3Ecdi_FETCH-hal_primary_oai_HAL_hal_00483243v13%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true