On Thu, May 4, 2023 at 8:14=E2=80=AFAM Alan = Shusterman alan[-]reed.edu <owner-chemistry _ ccl.net> wrote:

ChatGPT's answer contains some correct information,= =20 but it is not "fine". It is incomplete and it can lead many reade= rs to incorrect conclusions.

First, ChatGPT provid= es an incomplete description of methylamine, "one nitrogen atom and one= =20 methyl group". That phrase adds up to N-CH3. 2 H atoms are missing.

Second, most hydrogen bonds connect a hydrogen b= ond donor and a hydrogen bond acceptor, See Wikipedia, https://en.wikipedia.= org/wiki/Hydrogen_bond
ChatGPT fails to describe either of these participants properly. It only mentions = one property of the nitrogen (lone pair), and it does not describe any requ= ired properties of=20 hydrogen (see below).

Nitrogen properties. ChatGPT= mentions lone pairs. Unfortunately, lone pairs are not a sufficient basis = for=20 an answer. F in HF has 3 lone pairs but is a weak hydrogen bond acceptor, w= hereas F in F anion (4 lone pairs) is a much stronger hydrogen bond acceptor. But don't be misled because Ne= (also 4 lone pairs) is not a hydrogen bond acceptor. We cannot simply rely= on lone pairs.

Hydrogen properties. ChatGPT m= entions "hydrogen". That is correct. Hydrogens are always found in hydrogen bond donors, but not every hydrogen atom form= s=20 hydrogen bonds. Usually the hydrogen must carry a partial positive=20 charge, and this is usually achieved by H being bonded to a more=20 electronegative atom. ChatGPT does not even specify which hydrogen=20 participates in the hydrogen bond. While it is tempting to assume that=20 it's implied because the=20 hydrogen bond occurs between methylamine and pyrazine, that doesn't do = the job because ChatGPT's description=20 of methylamine is incomplete. It states only that "the hydrogen atom in methylamine can form a hydrogen bond", but there are = 5 H in methylamine. ChatGPT seems to think there are only 3H because it say= s methylamine contains "one nitrogen atom and one methyl group".<= br>

Here's another ChatGPT=20 example that reached me a few weeks ago that has no bearing on this thread&= #39;s conversation around H bonding.=C2=A0 A chemistry teacher and friend (= who will=20 remain anonymous) asked ChatGPT to "explain the NMR spectrum of = ethyl acetate" and sent me ChatGPT's answer:

Ethyl acetate is a=20 common organic compound with the chemical formula CH3COOCH2CH3. Its=20 nuclear magnetic resonance (NMR) spectrum displays characteristic peaks=20 corresponding to the different types of protons present in the molecule. In the proton NMR spectrum of ethyl acetate, there are four types of protons: the two methyl group protons (CH3),=20 the methylene group proton adjacent to the carbonyl (C=3DO) group (CH2),=20 and the carbonyl group proton (C=3DO). The chemical shifts and splitting=20 patterns of these protons are as follows:
=C2=A0 =C2=A0 =E2=80=A2 The two methyl group protons appear as a singlet pe= ak at around=20 1.25 ppm (parts per million), which is typical of alkyl methyl protons.
=C2=A0 =C2=A0 =E2=80=A2 The methylene group proton adjacent to the carbonyl= group appears=20 as a triplet peak at around 4.1 ppm, with a coupling constant of about 7 Hz. This triplet splitting arises from the coupling of the methylene=20 proton with the two equivalent methyl group protons.
=C2=A0 =C2=A0 =E2=80=A2 The carbonyl group proton appears as a singlet peak= at around 2.05 ppm, which is typical of carbonyl protons.
Overall, the NMR spectrum of ethyl acetate displays four peaks, each corresponding to a different type of proton=20 in the molecule. By analyzing the chemical shifts and splitting patterns of these peaks, it is possible to identify the different types of=20 protons in ethyl acetate and obtain information a= bout the molecular structure and bonding.

= The so-called explanation (much like the previous one regarding methy= lamine and pyrazine) is a mixed bag. There is good and there is bad. And ev= en when there is good, ChatGPT uses it incorrectly.
Example of good info: a correct formula for ethyl acetate.
=
Some examples of bad inferences:
- "= carbonyl group proton" does not exist in this molecule
- there=20 are six, not "two" methyl group protons in the formula
- the formula shows two methylene group protonS, not a "m= ethylene group proton"
- the methyl groups are = inequivalent and produce signals at different chemical shifts whereas ChatG= PT says there is one signal that is due to "two methyl group protons&q= uot; and describes them both as "alkyl methyl protons" (actually,= one is an alkyl methyl, the other is an acyl methyl)
- many errors in t= he coupling patterns and explanations of coupling
And a final conclusion that is highly misleading:=
- "the NMR spectrum of ethyl acetate displ= ays four peaks"
No. There are actually 3 types = of protons, and they produce these signal patterns: a singlet (1 peak), a t= riplet (3 peaks) and a quartet (4 peaks) for a total of 8 peaks.
ChatGPT's conclusion (4 peaks) doesn't even agree with= its own analysis. It lists 3 types of protons, and identifies them as prod= ucing two singlets + one triplet -> 3 signals or 5 peaks.

Obviously, this is a much worse ex= ample of ChatGPT's abilities than the previous one, but I think they ha= ve much in common. Tread carefully.

<= /div>
Alan

On Wed, May 3, 2023 at 1:12=E2= =80=AFPM Kshatresh Dutta Dubey kshatresh_+_gmail.com <owner-chemistry**ccl.net> wrote:
=
I am pasting answer from ChatGPT = which seems fine to me:
"Yes, it is possible for a hydrogen bond to form = between pyrazine and methylamine.
Pyrazine is a six-membered aromatic heterocycle = containing two nitrogen atoms in its ring structure, while methylamine is a= simple amine molecule with one nitrogen atom and one methyl group.
In the case of= hydrogen bonding, the hydrogen atom in methylamine can form a hydrogen bon= d with one of the nitrogen atoms in pyrazine. This can occur because nitrog= en has a lone pair of electrons, which can form a hydrogen bond with hydrog= en."
Hope it helps.
<= div dir=3D"auto">KDD

--
Dr. = Partha Sarathi Sengupta
Associate Professor
Vivekananda Mahavidyalaya= , Burdwan