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I would like to be able to modify the angular position of the foreground atoms in the Newman projection: in the documentation, I only saw the modification of the angle for the carbon of the second plane.

Does somebody have an idea ?

Nicolas
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  • 3
    Please provide a MWE. A picture would help also, indicating exactly what you want to change. – Sandy G Feb 08 '23 at 17:08
  • @Nicolas … sorry. The manual clearly states on page 27 top right under \newman that the angle only rotates the atoms on the back. So the three axes in the front are fixed. The only way to adjust those is to create your own tikzpicture environment where you can rotate them too. – alchemist Feb 08 '23 at 17:26

1 Answers1

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Well, I gave this question some thought. Actually it is unnecessary to be able to change the angle of the three frontal atoms in a Newman projection. As why that is so, let's first see what a Newman projections actually is.

In a Newman projection you visualize the orientation of substituents on two adjacent tetrahedral carbon atoms. So the frontal substituents are taken as fixed and by rotation of carbon-carbon axis you can see how the substituents on the second backside carbon atom interact with the frontal substituents. In essence you can visualize steric hindrance and explain energy fluctuations in that rotation.

If you want to rotate the substituents on the frontal carbon atom, you simply switch the point of view along the axis, making the frontal one now the backside carbon atom.

When you are dealing with other than tetrahedral atoms a Newman projection is exchanged for a Fischer projection. Where the Newman projection focuses on the spatial stereochemistry, the Fisher projection focuses on the geometric stereochemistry. So where you can tell whether a structure is eclipsed or staggered in a Newman projection, you can tell if a structure has cis or trans orientation in a Fisher projection.

EDIT

As seen in the comments the OP has a specific application of the Newman projection in mind. This small MWE uses the pic option to pass arguments to a drawing. the angles can now arbitrary chosen to draw a Newman projection:

\documentclass[11pt]{article}

\usepackage[a4paper,margin=2cm]{geometry}

\usepackage{tikz} \usetikzlibrary{decorations,decorations.markings,decorations.pathmorphing,backgrounds,calc,shapes.geometric,shapes.misc}

\begin{document}

    \begin{tikzpicture}
        [pics/arms/.style args={#1,#2,#3}{code={\draw  plot[polar comb, mark=*] coordinates { (#1:2) (#2:2) (#3:2)};}}
        ]
    \begin{scope}[on background layer, thick]
        \draw[blue] (0,0) pic {arms={25,45,75}};
        \filldraw[black!10] (0,0) circle[radius=1];
    \end{scope}

    \begin{scope}[thick]    
        \draw[red] (0,0) pic {arms={180,225,315}};
        \filldraw[black] (0,0) circle[radius=0.2];
    \end{scope}
\end{tikzpicture}   

\end{document}

Resulting in: newman-angle

Adding the option to label the positions with groups using the chemmacros package and its options, the code becomes:

\documentclass[11pt]{article}

\usepackage[a4paper,margin=2cm]{geometry}

\usepackage{tikz} \usetikzlibrary{decorations,decorations.markings,decorations.pathmorphing,backgrounds,calc,shapes.geometric,shapes.misc}

\usepackage[charter]{mathdesign} \usepackage[minimal]{chemmacros} \chemsetup{greek=mathdesign,formula=chemformula} \chemsetup[chemformula]{format={\sffamily}}

\begin{document}

    \begin{tikzpicture}
        [pics/arms/.style args={#1,#2,#3}{code={\draw  plot[polar comb, mark=*] coordinates { (#1:2) (#2:2) (#3:2)};
            \draw plot coordinates {(#1:2.5)} node(atm1) {};
            \draw plot coordinates {(#2:2.5)} node(atm2) {};
            \draw plot coordinates {(#3:2.5)} node(atm3) {};
        }}
        ]
    \begin{scope}[on background layer, thick]
        \draw[blue] (0,0) pic {arms={25,45,75}};
        \filldraw[black!10] (0,0) circle[radius=1];
        \node at (atm1) {\ch{CH3}};
        \node at (atm2) {\ch{C2H5}};
        \node at (atm3) {\ch{H}};
    \end{scope}

    \begin{scope}[thick]    
        \draw[red] (0,0) pic {arms={180,225,315}};
        \filldraw[black] (0,0) circle[radius=0.2];
        \node at (atm1) {\ch{CH3}};
        \node at (atm2) {\ch{H}};
        \node at (atm3) {\ch{Cl}};
    \end{scope}
\end{tikzpicture}   

\end{document}

which results in: newman_groups

alchemist
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  • I know that chemically it is equivalent to turn the rear carbon instead of the front carbon. Except that pedagogically, it's not quite the same and before going any further, I would also have preferred to be able to modify the angle of the front carbon. – Nicolas Feb 08 '23 at 21:05
  • Well, you have something specifically in mind as to why you want to have that option? Your remark made me curious – alchemist Feb 08 '23 at 22:23
  • I have some students who are new to organic chemistry: already, knowing that bonds can "freely" rotate challenges them. They have a vision in space that is sometimes complicated so if I also have to tell them to turn the whole molecule to ensure that on the front carbon the grouping has to be at the top instead of at the bottom, it is complicated! – Nicolas Feb 08 '23 at 22:25
  • Ah, that sounds like the textbook "dictate" I noticed in my students. They see one 2D projection of a structure (or space filled drawing) and are unable to rotate that in their mind. They see - so to speak - only the architectural top view, but not the side or front view of that structure. But when you are writing a document explaining the variation in angles and bound lengths due to vibration, rotation and energy fluctuations, you still represent those changes in bounds as a 2D figure. Wouldn't a 3D program offer a better insight in spatial variation? – alchemist Feb 09 '23 at 10:15
  • I'm doing a course on Newman's representation so I have no choice ;) – Nicolas Feb 09 '23 at 11:01
  • As I said, I am intrigued by your question. Was searching on the pic option in TikZ to see if that could be used to draw Newman projections with changing bound angles. In fact: I need to edit my answer as the Newman module in chemmacros is showing ideal angles only. Bulky groups and/or polar bounds will distort the angles in that ideal situation. – alchemist Feb 09 '23 at 11:06