Is phosphorine (C₅H₅P) aromatic?











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Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



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    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    Nov 23 at 16:23















up vote
10
down vote

favorite












Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here










share|improve this question




















  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    Nov 23 at 16:23













up vote
10
down vote

favorite









up vote
10
down vote

favorite











Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here










share|improve this question















Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here







aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds






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edited Nov 24 at 19:50









Mithoron

3,64382844




3,64382844










asked Nov 23 at 15:34









user137644

1025




1025








  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    Nov 23 at 16:23














  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    Nov 23 at 16:23








2




2




Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23




Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
Nov 23 at 16:23










1 Answer
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up vote
13
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accepted










Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






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  • With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
    – Martin - マーチン
    Dec 4 at 16:38










  • So ... you apparently think this is not aromatic?
    – Oscar Lanzi
    Dec 5 at 0:38










  • No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
    – Martin - マーチン
    Dec 5 at 9:22











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1 Answer
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1 Answer
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active

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up vote
13
down vote



accepted










Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






share|improve this answer























  • With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
    – Martin - マーチン
    Dec 4 at 16:38










  • So ... you apparently think this is not aromatic?
    – Oscar Lanzi
    Dec 5 at 0:38










  • No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
    – Martin - マーチン
    Dec 5 at 9:22















up vote
13
down vote



accepted










Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






share|improve this answer























  • With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
    – Martin - マーチン
    Dec 4 at 16:38










  • So ... you apparently think this is not aromatic?
    – Oscar Lanzi
    Dec 5 at 0:38










  • No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
    – Martin - マーチン
    Dec 5 at 9:22













up vote
13
down vote



accepted







up vote
13
down vote



accepted






Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






share|improve this answer














Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.







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edited Nov 24 at 21:15









Waylander

5,2761719




5,2761719










answered Nov 23 at 16:26









Oscar Lanzi

14.3k12546




14.3k12546












  • With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
    – Martin - マーチン
    Dec 4 at 16:38










  • So ... you apparently think this is not aromatic?
    – Oscar Lanzi
    Dec 5 at 0:38










  • No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
    – Martin - マーチン
    Dec 5 at 9:22


















  • With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
    – Martin - マーチン
    Dec 4 at 16:38










  • So ... you apparently think this is not aromatic?
    – Oscar Lanzi
    Dec 5 at 0:38










  • No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
    – Martin - マーチン
    Dec 5 at 9:22
















With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン
Dec 4 at 16:38




With reference you mean the Wikipedia article? I have quite a bit of trouble believing this answer without knowing the context in which these 88% of aromatic character came about. Since there isn't even an agreed-upon rigorous definition of aromaticity, the number is without context equally as informative as a picked number from the phone book.
– Martin - マーチン
Dec 4 at 16:38












So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38




So ... you apparently think this is not aromatic?
– Oscar Lanzi
Dec 5 at 0:38












No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン
Dec 5 at 9:22




No, that is not what I said. I just don't have any trust in that assessment of the 88% without any context of how this number came about.
– Martin - マーチン
Dec 5 at 9:22


















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