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wolfx
(Hive Bee)
10-24-04 22:07
No 537528
User Picture       Sulfate salt

I think in the hydrochloride salt, the hydrogen in the HCl forms a hydrogen bond with the nitrogen in the MDMA molecule, correct ?

Now, I am not sure what kind of bond it is formed in the sulfate salt. BTW, is it written 2(MDMA).SO4, is this correct ? Is it a normal covalent bond ? ( I don't think so )

indole_amine
(Hive Bee)
10-25-04 11:42
No 537668
User Picture       complex salt, not ionic

Both HCl and sulfate salt are complex salts, meaning their ions aren't held together by the usual ionic forces but rather just by weak forces like dipole/dipole or van-der-waals or (in this case) H-bridge bonds. This kind of intermolecular force can be seen with molecules containing N or O bearing one ore more hydrogens (like NH2 for example).

Therefore, the correct formula are:

MDMA*HCl   or   (MDMA)2*H2SO4

(each hydrogen from the acid attracts one amine nitrogen, which becomes partially positive, depicted through "delta+" at the nitrogen and "delta-" at the hydrogen bearing counterpart, i.e. Cl or SO4)

Because the hydrogen bond is rather weak compared to electron sharing bonds, complex salts are usually not very stable, compared to ionic bonds (like with NaCl) or electron sharing bonds (which are called covalent bonds).

_{indole_amine}

hypo
(Balanced Ego)
10-25-04 12:12
No 537675
      what?

> Both HCl and sulfate salt are complex salts, meaning their ions aren't
> held together by the usual ionic forces but rather just by weak forces
> like dipole/dipole or van-der-waals or (in this case) H-bridge bonds.

wtf? i have never heard of this.
of course it's ionic forces between MDMAH+ and Cl- resp. MDMAH+ and HSO4- or SO4--.

could you please provide a pointer detailing the "complex salt"-thingy? textbook
or otherwise? i think you are confusing this with hydro-complexes as in CaSO4.2H2O.
(those aren't H-bridges either, but dative bonds)

ps: for a great book about bonds, complexes and all that stuff, check out
"Inorganic Chemistry: Principles of Structure and Reactivity" by Huheey.
very recommended.

HÎ¨=EÎ¨

indole_amine
(Hive Bee)
10-25-04 12:59
No 537679
User Picture       intramolecular forces..

"Hydrogen Bonding
A hydrogen bond is not a covalent bond but a particularly strong transient dipole-dipole interaction. A hydrogen atom can participate in hydrogen bonding if it is linked covalently to an electronegative atom such as oxygen, nitrogen or fluorine. Hydrogen bonding is a strong intermolecular interaction, requiring ~5kcal mol-1 to break (c.f. ~100kcal mol-1 required to break a C–H or N–H covalent bond). Hydrogen bonding is replete in nature (i.e. DNA base pairing) and has a large effect upon the physical properties of organic compounds."

from http://users.ox.ac.uk/~mwalter/web_04/year1/intro/forces.htm
(utf google..)

Also good:

http://itl.chem.ufl.edu/2045/lectures/lec_g.html

http://www.uni-giessen.de/chemie/vorlesung/einfuehrung_oc/4000main.htm

http://onsager.bd.psu.edu/~jircitano/IMforces.html

_{indole_amine}

indole_amine
(Hive Bee)
10-25-04 13:14
No 537680
User Picture       example for H bonding in complex salt

"An Intriguing Hydrogen Bond Pattern in a Maleate Salt. Connie G. Chidester, Michael S. Bergren and Richard F. Heier, Pharmacia & Upjohn, Kalamazoo, MI

PNU-95666E is a dopamine D 2 agonist currently in Phase II Clinical trials for acute treatment of Parkinson’s disease. Although during several years of preclinical testing it was widely perceived in the research community as an important and interesting compound, it was unusually difficult to crystallize and the crystal structure was done only recently. PNU-95666E is the (R) isomer of a methylamino-imidazoquinolinone, (5-(methylamino)-5,6-dihydro-4H-imidazo {4,5,1-ij} quinolin-2(1H)-one). The (R)-dipropylamino analog PNU-86170 crystallizes readily as either the free base or a salt and a crystal structure had been done of the hydrobromide. However, suitable crystals of the free base of PNU-95666 could not be obtained, and of the many salts tried, including hydrochloride, hydrobromide, fumarate, maleate and various hydrates of these, only the maleate salts seemed at all amenable to crystallization. After considerable effort, diffraction quality crystals were eventually obtained of the maleate.

The crystal structure is triclinic, spacegroup P1, with two molecules in the asymmetric unit and an equal number of maleic acid molecules. The hydrogen bonding pattern is complex and beautiful and offers many clues toward understanding why the compound was so difficult to crystallize and why the maleic acid salt was the key to crystallization. Hydrogen bonding patterns involving maleates in other crystal structures are compared."

(http://www.hwi.buffalo.edu/ACA/ACA99/abstracts/text/W0237.html)

_{indole_amine}

hypo
(Balanced Ego)
10-25-04 13:48
No 537686
      and?

very cute, but:
i didn't ask you for the definition of H-bridges (which i know well), but for
the definition of "complex salts" and why you think that MDMA.HCl is such a beast.

HÎ¨=EÎ¨

indole_amine
(Hive Bee)
10-25-04 15:10
No 537698
User Picture       *

Firstly, I didn't answer any question about which type of bonds do keep complex salts together (it differs with different salts), but rather responded to your statement "of course it's ionic forces between MDMAH+ and Cl- resp. MDMAH+ and HSO4- or SO4--.". Because it is not ionic but H-bond forces.

Secondly, complex salts are those carrying a "*" in their name. This little sign depicts that the part on the left is complexed with the part on the right. Like with MDMA*HCl (ever saw Na*Cl?? Nope. Amine*HCl? D'oh - very common..)
Look it up for yourself whereever you like.

_{indole_amine}

hypo
(Balanced Ego)
10-25-04 15:27
No 537701
      you're mistaken

when people write MDMA.HCl, they don't mean that it's a complex. it's
just a lazy notation.
think about it: MDMA is a (broensted) base, HCl is a strong broensted
acid. do you really believe that in MDMA.HCl the proton stays with the HCl?
that's completely illogical.

complexes are what you get when you react a lewis acid with a lewis base.
(due to the lone pair amines are lewis bases too, but i don't see how HCl
would be a lewis acid.)

> Look it up for yourself whereever you like.

did you invent this expression? if not, then just tell me from where you got it.

HÎ¨=EÎ¨

moo
(Hive Addict)
10-25-04 16:20
No 537710
      Let's take an example: methylamine forms a...

Let's take an example: methylamine forms a salt which is often called methylamine hydrochloride (MeNH₂*HCl), which in fact means the same thing as methylammonium chloride (MeNH₃Cl, can also be expressed as an ion pair MeNH₃⁺Cl^-). I guess you could even call ammonium chloride with the name ammonia hydrochloride and mark it as NH₃*HCl. Why would MDMA be any different?

I assume that complex salt means an ion pair of a charged complex and some counter ion. A few randomly picked inorganic examples:
3Zn²⁺(aq) + 2[Fe(CN)₆]^3-(aq) --> Zn₃[Fe(CN)₆]₂(s)
Al(OH)₃(s) + KOH(aq) --> [Al(OH)₄]^-(aq) + K⁺(aq)

Maybe one could call any of the above amine salts a complex salt. An amine and a proton complex with each other to form an ammonium ion (lewis base + lewis acid), our complex ion. When this is done with HCl, we have the Cl^- ion as the counter ion for the complex ion. When this ion pair, a salt, crystallizes, the crystal lattice includes both the ammonium ions and the chloride ions, in 1:1 ratio. So maybe you can call it a complex salt. It is just a word, it doesn't rule out ionic bonds in the crystal lattice in any way. Similarly writing MDMA*HCl is just a way to describe a salt, MDMAH⁺Cl^-.

_{fear fear hate hate}

Nicodem
(Hive Bee)
10-25-04 16:53
No 537717
User Picture       Salts are salts whether organic or inorganic

I don't want to anger anybody but hypo and moo are right. MDMA or other amine salts are ionic salts just like NaCl or other inorganic salts. Actually, you could even call the quarternary nitrogen cation R₃NH⁺ that result from their protonation a "Lewis complex". That's because a proton is a Lewis acid (it accepts electron pairs) and R₃N: is a Lewis base (it donates the electron pair). It all depends on whether you prefer the Lewis or Bronstead acid-base definitions and concepts.
The resulting salts like amine hydrochlorides, sulphates and even acetates are all bonded by ionic interactions between the cations and anions, hence they are usually crystalline solids. H-bonds or dipol-dipol interactions are something else and their energy of interaction is several magnitudes lower when compared to the ionic 'bond'.

�The real drug-problem is that we need more and better drugs.� � J. Ott

hypo
(Balanced Ego)
10-25-04 16:56
No 537718
      hm yeah...

> An amine and a proton complex with each other to form an ammonium ion
> (lewis base + lewis acid), our complex ion.

you've got a point there.

but while technically H+ is a lewis acid, it's an exception in that
you wouldn't call an ammonium compound a complex. all Hs on the nitrogen
are equivalent, so it's just a covalent bond. (ok, you could say that N---
is a quadruple lewis base, but this would be quite a stretch, wouldn't it?)
for this type of compound the lewis acid/base theory just doesn't fly as
well as the broensted one (yeah, i know - lewis is a superset of broensted).

and even if you call it a complex, the correct way to write it would be
[MDMA*H]Cl or something like that. or Na[CH3COO*H]. i don't think i could
get used to this. wink

so imho MDMA*HCl or MeNH2*HCl is slightly wrong. from a formal point of
view it describes what happens (MDMA gives an electron pair to HCl), but
it gives an incorrect picture of the actual electron configuration. (as
shown by indole_amine's confusion)

HÎ¨=EÎ¨

moo
(Hive Addict)
10-25-04 17:21
No 537722
      It was merely a thought play to illustrate how

It was merely a thought play to illustrate how the language and semantics are only there for communication. You can name a molecule in numerous ways for example, maybe detailing different aspects and points of view, but the actual molecule stays the same.

I see your point regarding the hydrogens on the amine though.

_{fear fear hate hate}

wolfx
(Hive Bee)
10-25-04 20:53
No 537770
User Picture       From my point of view, main problem is that I...

From my point of view, main problem is that I was missing the two H's in the H2SO4. So it is very similar to the HCl salt case.

Thanks to indole_amine for explaining that the two H's are there also.

Just in case, other projects etc. apparently going well, again busy with work, will keep you informed.

W.

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	All 13 posts		Subject: Sulfate salt		Please login to post		Down


		wolfx (Hive Bee) 10-24-04 22:07 No 537528				Sulfate salt
						I think in the hydrochloride salt, the hydrogen in the HCl forms a hydrogen bond with the nitrogen in the MDMA molecule, correct ? Now, I am not sure what kind of bond it is formed in the sulfate salt. BTW, is it written 2(MDMA).SO4, is this correct ? Is it a normal covalent bond ? ( I don't think so )



		indole_amine (Hive Bee) 10-25-04 11:42 No 537668				complex salt, not ionic
						Both HCl and sulfate salt are complex salts, meaning their ions aren't held together by the usual ionic forces but rather just by weak forces like dipole/dipole or van-der-waals or (in this case) H-bridge bonds. This kind of intermolecular force can be seen with molecules containing N or O bearing one ore more hydrogens (like NH2 for example). Therefore, the correct formula are: MDMAHCl or (MDMA)2H2SO4 (each hydrogen from the acid attracts one amine nitrogen, which becomes partially positive, depicted through "delta+" at the nitrogen and "delta-" at the hydrogen bearing counterpart, i.e. Cl or SO4) Because the hydrogen bond is rather weak compared to electron sharing bonds, complex salts are usually not very stable, compared to ionic bonds (like with NaCl) or electron sharing bonds (which are called covalent bonds). _{indole_amine}



		hypo (Balanced Ego) 10-25-04 12:12 No 537675				what?
						> Both HCl and sulfate salt are complex salts, meaning their ions aren't > held together by the usual ionic forces but rather just by weak forces > like dipole/dipole or van-der-waals or (in this case) H-bridge bonds. wtf? i have never heard of this. of course it's ionic forces between MDMAH+ and Cl- resp. MDMAH+ and HSO4- or SO4--. could you please provide a pointer detailing the "complex salt"-thingy? textbook or otherwise? i think you are confusing this with hydro-complexes as in CaSO4.2H2O. (those aren't H-bridges either, but dative bonds) ps: for a great book about bonds, complexes and all that stuff, check out "Inorganic Chemistry: Principles of Structure and Reactivity" by Huheey. very recommended. HÎ¨=EÎ¨



		indole_amine (Hive Bee) 10-25-04 12:59 No 537679				intramolecular forces..
						"Hydrogen Bonding A hydrogen bond is not a covalent bond but a particularly strong transient dipole-dipole interaction. A hydrogen atom can participate in hydrogen bonding if it is linked covalently to an electronegative atom such as oxygen, nitrogen or fluorine. Hydrogen bonding is a strong intermolecular interaction, requiring ~5kcal mol-1 to break (c.f. ~100kcal mol-1 required to break a C–H or N–H covalent bond). Hydrogen bonding is replete in nature (i.e. DNA base pairing) and has a large effect upon the physical properties of organic compounds." from http://users.ox.ac.uk/~mwalter/web_04/year1/intro/forces.htm (utf google..) Also good: http://itl.chem.ufl.edu/2045/lectures/lec_g.html http://www.uni-giessen.de/chemie/vorlesung/einfuehrung_oc/4000main.htm http://onsager.bd.psu.edu/~jircitano/IMforces.html _{indole_amine}



		indole_amine (Hive Bee) 10-25-04 13:14 No 537680				example for H bonding in complex salt
						"An Intriguing Hydrogen Bond Pattern in a Maleate Salt. Connie G. Chidester, Michael S. Bergren and Richard F. Heier, Pharmacia & Upjohn, Kalamazoo, MI PNU-95666E is a dopamine D 2 agonist currently in Phase II Clinical trials for acute treatment of Parkinson’s disease. Although during several years of preclinical testing it was widely perceived in the research community as an important and interesting compound, it was unusually difficult to crystallize and the crystal structure was done only recently. PNU-95666E is the (R) isomer of a methylamino-imidazoquinolinone, (5-(methylamino)-5,6-dihydro-4H-imidazo {4,5,1-ij} quinolin-2(1H)-one). The (R)-dipropylamino analog PNU-86170 crystallizes readily as either the free base or a salt and a crystal structure had been done of the hydrobromide. However, suitable crystals of the free base of PNU-95666 could not be obtained, and of the many salts tried, including hydrochloride, hydrobromide, fumarate, maleate and various hydrates of these, only the maleate salts seemed at all amenable to crystallization. After considerable effort, diffraction quality crystals were eventually obtained of the maleate. The crystal structure is triclinic, spacegroup P1, with two molecules in the asymmetric unit and an equal number of maleic acid molecules. The hydrogen bonding pattern is complex and beautiful and offers many clues toward understanding why the compound was so difficult to crystallize and why the maleic acid salt was the key to crystallization. Hydrogen bonding patterns involving maleates in other crystal structures are compared." (http://www.hwi.buffalo.edu/ACA/ACA99/abstracts/text/W0237.html) _{indole_amine}



		hypo (Balanced Ego) 10-25-04 13:48 No 537686				and?
						very cute, but: i didn't ask you for the definition of H-bridges (which i know well), but for the definition of "complex salts" and why you think that MDMA.HCl is such a beast. HÎ¨=EÎ¨



		indole_amine (Hive Bee) 10-25-04 15:10 No 537698				*
						Firstly, I didn't answer any question about which type of bonds do keep complex salts together (it differs with different salts), but rather responded to your statement "of course it's ionic forces between MDMAH+ and Cl- resp. MDMAH+ and HSO4- or SO4--.". Because it is not ionic but H-bond forces. Secondly, complex salts are those carrying a "" in their name. This little sign depicts that the part on the left is complexed with the part on the right. Like with MDMAHCl (ever saw NaCl?? Nope. AmineHCl? D'oh - very common..) Look it up for yourself whereever you like. _{indole_amine}



		hypo (Balanced Ego) 10-25-04 15:27 No 537701				you're mistaken
						when people write MDMA.HCl, they don't mean that it's a complex. it's just a lazy notation. think about it: MDMA is a (broensted) base, HCl is a strong broensted acid. do you really believe that in MDMA.HCl the proton stays with the HCl? that's completely illogical. complexes are what you get when you react a lewis acid with a lewis base. (due to the lone pair amines are lewis bases too, but i don't see how HCl would be a lewis acid.) > Look it up for yourself whereever you like. did you invent this expression? if not, then just tell me from where you got it. HÎ¨=EÎ¨



		moo (Hive Addict) 10-25-04 16:20 No 537710				Let's take an example: methylamine forms a...
						Let's take an example: methylamine forms a salt which is often called methylamine hydrochloride (MeNH₂HCl), which in fact means the same thing as methylammonium chloride (MeNH₃Cl, can also be expressed as an ion pair MeNH₃⁺Cl^-). I guess you could even call ammonium chloride with the name ammonia hydrochloride and mark it as NH₃HCl. Why would MDMA be any different? I assume that complex salt means an ion pair of a charged complex and some counter ion. A few randomly picked inorganic examples: 3Zn²⁺(aq) + 2[Fe(CN)₆]^3-(aq) --> Zn₃[Fe(CN)₆]₂(s) Al(OH)₃(s) + KOH(aq) --> [Al(OH)₄]^-(aq) + K⁺(aq) Maybe one could call any of the above amine salts a complex salt. An amine and a proton complex with each other to form an ammonium ion (lewis base + lewis acid), our complex ion. When this is done with HCl, we have the Cl^- ion as the counter ion for the complex ion. When this ion pair, a salt, crystallizes, the crystal lattice includes both the ammonium ions and the chloride ions, in 1:1 ratio. So maybe you can call it a complex salt. It is just a word, it doesn't rule out ionic bonds in the crystal lattice in any way. Similarly writing MDMA*HCl is just a way to describe a salt, MDMAH⁺Cl^-. _{fear fear hate hate}



		Nicodem (Hive Bee) 10-25-04 16:53 No 537717				Salts are salts whether organic or inorganic
						I don't want to anger anybody but hypo and moo are right. MDMA or other amine salts are ionic salts just like NaCl or other inorganic salts. Actually, you could even call the quarternary nitrogen cation R₃NH⁺ that result from their protonation a "Lewis complex". That's because a proton is a Lewis acid (it accepts electron pairs) and R₃N: is a Lewis base (it donates the electron pair). It all depends on whether you prefer the Lewis or Bronstead acid-base definitions and concepts. The resulting salts like amine hydrochlorides, sulphates and even acetates are all bonded by ionic interactions between the cations and anions, hence they are usually crystalline solids. H-bonds or dipol-dipol interactions are something else and their energy of interaction is several magnitudes lower when compared to the ionic 'bond'. �The real drug-problem is that we need more and better drugs.� � J. Ott



		hypo (Balanced Ego) 10-25-04 16:56 No 537718				hm yeah...
						> An amine and a proton complex with each other to form an ammonium ion > (lewis base + lewis acid), our complex ion. you've got a point there. but while technically H+ is a lewis acid, it's an exception in that you wouldn't call an ammonium compound a complex. all Hs on the nitrogen are equivalent, so it's just a covalent bond. (ok, you could say that N--- is a quadruple lewis base, but this would be quite a stretch, wouldn't it?) for this type of compound the lewis acid/base theory just doesn't fly as well as the broensted one (yeah, i know - lewis is a superset of broensted). and even if you call it a complex, the correct way to write it would be [MDMAH]Cl or something like that. or Na[CH3COOH]. i don't think i could get used to this. so imho MDMAHCl or MeNH2HCl is slightly wrong. from a formal point of view it describes what happens (MDMA gives an electron pair to HCl), but it gives an incorrect picture of the actual electron configuration. (as shown by indole_amine's confusion) HÎ¨=EÎ¨



		moo (Hive Addict) 10-25-04 17:21 No 537722				It was merely a thought play to illustrate how
						It was merely a thought play to illustrate how the language and semantics are only there for communication. You can name a molecule in numerous ways for example, maybe detailing different aspects and points of view, but the actual molecule stays the same. I see your point regarding the hydrogens on the amine though. _{fear fear hate hate}



		wolfx (Hive Bee) 10-25-04 20:53 No 537770				From my point of view, main problem is that I...
						From my point of view, main problem is that I was missing the two H's in the H2SO4. So it is very similar to the HCl salt case. Thanks to indole_amine for explaining that the two H's are there also. Just in case, other projects etc. apparently going well, again busy with work, will keep you informed. W.

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