Is phosphorine (C₅H₅P) aromatic?












11












$begingroup$


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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$endgroup$








  • 3




    $begingroup$
    Phosphinine is aromatic, but somewhat less than benzene.
    $endgroup$
    – mykhal
    Nov 23 '18 at 16:23
















11












$begingroup$


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







share|improve this question











$endgroup$








  • 3




    $begingroup$
    Phosphinine is aromatic, but somewhat less than benzene.
    $endgroup$
    – mykhal
    Nov 23 '18 at 16:23














11












11








11





$begingroup$


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







share|improve this question











$endgroup$




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




aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited Nov 24 '18 at 19:50









Mithoron

3,70882846




3,70882846










asked Nov 23 '18 at 15:34









user137644user137644

995




995








  • 3




    $begingroup$
    Phosphinine is aromatic, but somewhat less than benzene.
    $endgroup$
    – mykhal
    Nov 23 '18 at 16:23














  • 3




    $begingroup$
    Phosphinine is aromatic, but somewhat less than benzene.
    $endgroup$
    – mykhal
    Nov 23 '18 at 16:23








3




3




$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23




$begingroup$
Phosphinine is aromatic, but somewhat less than benzene.
$endgroup$
– mykhal
Nov 23 '18 at 16:23










1 Answer
1






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oldest

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13












$begingroup$

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











$endgroup$









  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 4 '18 at 16:38










  • $begingroup$
    So ... you apparently think this is not aromatic?
    $endgroup$
    – Oscar Lanzi
    Dec 5 '18 at 0:38






  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 5 '18 at 9:22












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1 Answer
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13












$begingroup$

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











$endgroup$









  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 4 '18 at 16:38










  • $begingroup$
    So ... you apparently think this is not aromatic?
    $endgroup$
    – Oscar Lanzi
    Dec 5 '18 at 0:38






  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 5 '18 at 9:22
















13












$begingroup$

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











$endgroup$









  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 4 '18 at 16:38










  • $begingroup$
    So ... you apparently think this is not aromatic?
    $endgroup$
    – Oscar Lanzi
    Dec 5 '18 at 0:38






  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 5 '18 at 9:22














13












13








13





$begingroup$

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











$endgroup$



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














share|improve this answer



share|improve this answer








edited Nov 24 '18 at 21:15









Waylander

6,73411424




6,73411424










answered Nov 23 '18 at 16:26









Oscar LanziOscar Lanzi

16.2k12749




16.2k12749








  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 4 '18 at 16:38










  • $begingroup$
    So ... you apparently think this is not aromatic?
    $endgroup$
    – Oscar Lanzi
    Dec 5 '18 at 0:38






  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 5 '18 at 9:22














  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 4 '18 at 16:38










  • $begingroup$
    So ... you apparently think this is not aromatic?
    $endgroup$
    – Oscar Lanzi
    Dec 5 '18 at 0:38






  • 1




    $begingroup$
    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.
    $endgroup$
    – Martin - マーチン♦
    Dec 5 '18 at 9:22








1




1




$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38




$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 4 '18 at 16:38












$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38




$begingroup$
So ... you apparently think this is not aromatic?
$endgroup$
– Oscar Lanzi
Dec 5 '18 at 0:38




1




1




$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22




$begingroup$
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.
$endgroup$
– Martin - マーチン♦
Dec 5 '18 at 9:22


















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