Sciencemadness Discussion Board

Neutral but not neutral

thesmug - 24-5-2014 at 18:12

I am sorry I can't think of this off the top of my head but this is killing me. What is the name of an organic compound with equal positive and negative charges within itself? I can't think of what I would search to find this and have tried but with no luck. I know one of you can help!

UnintentionalChaos - 24-5-2014 at 18:36

Zwitterion

alexleyenda - 24-5-2014 at 18:41

Yup. You could have searched amino acids, they are definitely the most important zwitterions with their NH3+ COO- groups.

[Edited on 25-5-2014 by alexleyenda]

thesmug - 24-5-2014 at 18:49

Ok thanks! Also, would nitro groups count as zwitterions?
[edit] also also, would diative bonds be zwitterions?

[Edited on 5/25/14 by thesmug]

alexleyenda - 24-5-2014 at 18:57

Hmm that is a really good question... it could be as it has at the same time a positive and a negative charge, yet the charges cannot be changed by the pH as it usually is the case with zwitterions so I think it is not a zwitterion, but I am not sure at all. Research time :p

[Edit] Of what I've seen, my guess was right, R-NO2 are not zwitterions as the charges are formal charges, not real complete ionic charges.

[Edit 2] Diative bonds are definitely not zwitterions, no charge is left at all once the bond is made

[Edited on 25-5-2014 by alexleyenda]

smaerd - 24-5-2014 at 20:06

Not to be nit-picky but I do believe a dipole still may exist in dative bonding and there is still a coloumbic or electrostatic 'charge', just not an ionic charge.

Oh those nitrogroups almost always got the poor general chemistry students in my school. I suppose the nitrogroup could be considered a zwitterion? Personally I don't think that's the best way to describe it though as the negative charge on the oxygens is delocalized. Then again look at carboxylates in amino acids, they have delocalized charge as well and obviously are considered zwitterions. Yea alexleyenda I do believe the term zwitterion is typically used to describe an acid base reaction. Granted nitro oxygens can be protonated... Not sure, I'll bet IUPAC had a big confusing debate about it at one point or another.

blogfast25 - 25-5-2014 at 09:01

Quote: Originally posted by smaerd  
I suppose the nitrogroup could be considered a zwitterion?


No, of course not. For a Zwitterion the positive and negative charges have to well separated, by several bonds. That's not the case for a nitro group.