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Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines
This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings: N -(4-hydroxybenzylidene)phenylethylamine ( 1 ) and N -(4-hydroxy-3-methoxybenzylidene)tyramine ( 2 ). Molecules of compound 1 , with just one phenolic OH group, adopted...
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| Published in: | Journal of chemical crystallography 2020-09, Vol.50 (3), p.206-211 |
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| Main Authors: | , , |
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| Language: | English |
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| container_end_page | 211 |
| container_issue | 3 |
| container_start_page | 206 |
| container_title | Journal of chemical crystallography |
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| creator | Chaves, Sebastián Pérez-Redondo, Adrián Quevedo, Rodolfo |
| description | This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings:
N
-(4-hydroxybenzylidene)phenylethylamine (
1
) and
N
-(4-hydroxy-3-methoxybenzylidene)tyramine (
2
). Molecules of compound
1
, with just one phenolic OH group, adopted an
anti
conformation, and were associated in zigzag chains with O–H···N hydrogen bonds between the azomethine fragment and the hydroxyl group. However, a gauche conformation was preferred by compound
2
, which contained two hydroxyl groups in aromatic rings. Molecules of
2
were arranged in a three-dimensional array through O–H···N and O–H···O hydrogen bonding interactions. The results highlighted the importance of OH positions in the aromatic ring for the structural behaviour of the Schiff bases derived from phenylethylamines.
Graphical Abstract
Molecules of Schiff bases containing the moiety ArCH=N–CH
2
CH
2
Ar with one or two hydroxyl groups in the
para
position in the aromatic rings are associated in zigzag chains in the solid state through O–H···N hydrogen bonding interactions. |
| doi_str_mv | 10.1007/s10870-019-00792-7 |
| format | article |
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N
-(4-hydroxybenzylidene)phenylethylamine (
1
) and
N
-(4-hydroxy-3-methoxybenzylidene)tyramine (
2
). Molecules of compound
1
, with just one phenolic OH group, adopted an
anti
conformation, and were associated in zigzag chains with O–H···N hydrogen bonds between the azomethine fragment and the hydroxyl group. However, a gauche conformation was preferred by compound
2
, which contained two hydroxyl groups in aromatic rings. Molecules of
2
were arranged in a three-dimensional array through O–H···N and O–H···O hydrogen bonding interactions. The results highlighted the importance of OH positions in the aromatic ring for the structural behaviour of the Schiff bases derived from phenylethylamines.
Graphical Abstract
Molecules of Schiff bases containing the moiety ArCH=N–CH
2
CH
2
Ar with one or two hydroxyl groups in the
para
position in the aromatic rings are associated in zigzag chains in the solid state through O–H···N hydrogen bonding interactions.</description><identifier>ISSN: 1074-1542</identifier><identifier>EISSN: 1572-8854</identifier><identifier>DOI: 10.1007/s10870-019-00792-7</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Aromatic compounds ; Chains ; Chemical bonds ; Chemistry ; Chemistry and Materials Science ; Crystallography and Scattering Methods ; Hydrogen bonding ; Hydrogen bonds ; Hydroxyl groups ; Imines ; Inorganic Chemistry ; Organometallic Chemistry ; Original Paper ; Phenylethylamine ; Physical Chemistry ; Single crystals ; Solid state</subject><ispartof>Journal of chemical crystallography, 2020-09, Vol.50 (3), p.206-211</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2019</rights><rights>Springer Science+Business Media, LLC, part of Springer Nature 2019.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2347-3a660b8fccdd4555d3f1210a0f88b5d16029f66e834128873eb315803fad44fc3</citedby><cites>FETCH-LOGICAL-c2347-3a660b8fccdd4555d3f1210a0f88b5d16029f66e834128873eb315803fad44fc3</cites><orcidid>0000-0003-3023-9576</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids></links><search><creatorcontrib>Chaves, Sebastián</creatorcontrib><creatorcontrib>Pérez-Redondo, Adrián</creatorcontrib><creatorcontrib>Quevedo, Rodolfo</creatorcontrib><title>Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines</title><title>Journal of chemical crystallography</title><addtitle>J Chem Crystallogr</addtitle><description>This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings:
N
-(4-hydroxybenzylidene)phenylethylamine (
1
) and
N
-(4-hydroxy-3-methoxybenzylidene)tyramine (
2
). Molecules of compound
1
, with just one phenolic OH group, adopted an
anti
conformation, and were associated in zigzag chains with O–H···N hydrogen bonds between the azomethine fragment and the hydroxyl group. However, a gauche conformation was preferred by compound
2
, which contained two hydroxyl groups in aromatic rings. Molecules of
2
were arranged in a three-dimensional array through O–H···N and O–H···O hydrogen bonding interactions. The results highlighted the importance of OH positions in the aromatic ring for the structural behaviour of the Schiff bases derived from phenylethylamines.
Graphical Abstract
Molecules of Schiff bases containing the moiety ArCH=N–CH
2
CH
2
Ar with one or two hydroxyl groups in the
para
position in the aromatic rings are associated in zigzag chains in the solid state through O–H···N hydrogen bonding interactions.</description><subject>Aromatic compounds</subject><subject>Chains</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Crystallography and Scattering Methods</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Hydroxyl groups</subject><subject>Imines</subject><subject>Inorganic Chemistry</subject><subject>Organometallic Chemistry</subject><subject>Original Paper</subject><subject>Phenylethylamine</subject><subject>Physical Chemistry</subject><subject>Single crystals</subject><subject>Solid state</subject><issn>1074-1542</issn><issn>1572-8854</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhYMoWKt_wNWA62iek3SpxUeh6KK6chHSTGKnTJOaZJDx1xsdwZ2b-4BzzuV-AJxjdIkRElcJIykQRHgGyzojUByACeaCQCk5OywzEgxizsgxOElpixCaSSIm4HUVurapVllnW2rsTe6jrbRvqoXPNu5CZ03f6Tiu2uQ2-FQFV-WPUD3CG-s_h5Jgvd1vrB86mzdDp3ett-kUHDndJXv226fg5e72ef4Al0_3i_n1EhpCmYBU1zVaS2dM0zDOeUMdJhhp5KRc8wbXiMxcXVtJGSZSCmrXFHOJqNMNY87QKbgYc_cxvPc2ZbUNffTlpCKMMsJ5-bWoyKgyMaQUrVP72O50HBRG6huiGiGqAlH9QFSimOhoSkXs32z8i_7H9QWiOHV_</recordid><startdate>20200901</startdate><enddate>20200901</enddate><creator>Chaves, Sebastián</creator><creator>Pérez-Redondo, Adrián</creator><creator>Quevedo, Rodolfo</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-3023-9576</orcidid></search><sort><creationdate>20200901</creationdate><title>Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines</title><author>Chaves, Sebastián ; Pérez-Redondo, Adrián ; Quevedo, Rodolfo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2347-3a660b8fccdd4555d3f1210a0f88b5d16029f66e834128873eb315803fad44fc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Chains</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Crystallography and Scattering Methods</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Hydroxyl groups</topic><topic>Imines</topic><topic>Inorganic Chemistry</topic><topic>Organometallic Chemistry</topic><topic>Original Paper</topic><topic>Phenylethylamine</topic><topic>Physical Chemistry</topic><topic>Single crystals</topic><topic>Solid state</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chaves, Sebastián</creatorcontrib><creatorcontrib>Pérez-Redondo, Adrián</creatorcontrib><creatorcontrib>Quevedo, Rodolfo</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of chemical crystallography</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chaves, Sebastián</au><au>Pérez-Redondo, Adrián</au><au>Quevedo, Rodolfo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines</atitle><jtitle>Journal of chemical crystallography</jtitle><stitle>J Chem Crystallogr</stitle><date>2020-09-01</date><risdate>2020</risdate><volume>50</volume><issue>3</issue><spage>206</spage><epage>211</epage><pages>206-211</pages><issn>1074-1542</issn><eissn>1572-8854</eissn><abstract>This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings:
N
-(4-hydroxybenzylidene)phenylethylamine (
1
) and
N
-(4-hydroxy-3-methoxybenzylidene)tyramine (
2
). Molecules of compound
1
, with just one phenolic OH group, adopted an
anti
conformation, and were associated in zigzag chains with O–H···N hydrogen bonds between the azomethine fragment and the hydroxyl group. However, a gauche conformation was preferred by compound
2
, which contained two hydroxyl groups in aromatic rings. Molecules of
2
were arranged in a three-dimensional array through O–H···N and O–H···O hydrogen bonding interactions. The results highlighted the importance of OH positions in the aromatic ring for the structural behaviour of the Schiff bases derived from phenylethylamines.
Graphical Abstract
Molecules of Schiff bases containing the moiety ArCH=N–CH
2
CH
2
Ar with one or two hydroxyl groups in the
para
position in the aromatic rings are associated in zigzag chains in the solid state through O–H···N hydrogen bonding interactions.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10870-019-00792-7</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3023-9576</orcidid></addata></record> |
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| issn | 1074-1542 1572-8854 |
| language | eng |
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| subjects | Aromatic compounds Chains Chemical bonds Chemistry Chemistry and Materials Science Crystallography and Scattering Methods Hydrogen bonding Hydrogen bonds Hydroxyl groups Imines Inorganic Chemistry Organometallic Chemistry Original Paper Phenylethylamine Physical Chemistry Single crystals Solid state |
| title | Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines |
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